Literature Report. Atroposelective Synthesis of Axially Chiral Arylpyrroles and Styrenes. : Zhong Yan : Ji Zhou :
|
|
|
- Lambert Fowler
- 5 years ago
- Views:
Transcription
1 Literature eport Atroposelective Synthesis of Axially Chiral ylpyrroles and Styrenes eporter Checker Date : Zhong Yan : Ji Zhou : Tan, B. et al. J. Am. Chem. Soc. 2017, 139, Tan, B. et al. at. Commun. 2017, 8,
2 Contents 1 ntroduction 2 Atroposelective Synthesis of Axially Chiral ylpyrroles 3 Atroposelective Synthesis of Axially Chiral Styrenes 4 Summary
3 CV of Bin Tan Education: M.S., Xiamen University Ph.D., anyang Technological University, Singapore Postdoc., The Scripps esearch nstitute Associate Professor., South University of Science and Bin Tan Technology esearch: 核心骨架结构导向的催化不对称合成 现代催化体系和绿色合成新方法的开发 金属与有机催化协同的催化体系应用 手性药物的开发和天然产物策略全合成 3
4 ntroduction ' H 2 CPA ( 10 mol%) '' LA ( 10 mol%) ' '' CPA 9-anthryl P H 9-anthryl Tan, B. et al. J. Am. Chem. Soc. 2017, 139, u H CH Amine ( 5 mol%) u CH H Amine = TPS, = 3,5- ( CH 3)2C 6 H 3 Tan, B. et al. at. Commun. 2017, 8,
5 Axially Chiral ylpyrroles Cl H Cl Cl H A Marinopyrrole Cl H Chiral arylpyrrole Me F 3 C H Ph Ph H Me B Murrastifoline-F C Amino alcohol chiral ligand
6 esolution of acemic ylpyrroles F 3 C C 2 H C 2 H H H 2 C 2 CH 3 EtH, rt, 2 h (S) -1 ( ) -2 (±) -1 () -2 ( a ) a q. a 2 C 3 (b) 15% aq. HCl F 3 C H Ph Ph 4 steps F 3 C C 2 H C 2 H (S) -3 69% yield, 99% ee (S) -1 80% yield, >96% ee Faigl, F. et al. Tetrahedron: Asymmetry 2011, 22, 1879.
7 Asymmetric Paal-Knorr eaction Paal-Knorr reaction ' H 2 id ' -H 2 id -H 2 ' H ' id H ' ' H 2 CPA ( 10 mol%) '' LA ( 10 mol%) ' '' CPA 9-anthryl P H 9-anthryl 30 examples up to 95% yield up to 97% ee Tan, B. et al. J. Am. Chem. Soc. 2017, 139, 1714.
8 Asymmetric Paal-Knorr eaction C 2 Me C 2 Me H 2 CPA ( 10 mol%) Solvent,T 1a 2a 3aa P H () -C1: = 9- phenanthryl () -C2: = 3,5- (CF 3)2C 6 H 3 (S) -C3: = 9-anthr yl (S) -C4: = 2,4,6- ( i Pr )3 C 6 H 2 (S) -C5: = 1- pyrenyl (S) -C6: = 1-na phthyl (S) -C7: = 4-ClC 6 H 4 P H () -C8: = 9- phenanthryl () -C9: = 9-anthr yl P H (S) -C10: = 9- phenanthryl Entry CPA T Solvent Yield (%) Ee (%) 1 ()-C1 rt CCl ()-C2 rt CCl (S)-C3 rt CCl (S)-C4 rt CCl (S)-C5 rt CCl (S)-C6 rt CCl (S)-C7 rt CCl
9 Asymmetric Paal-Knorr eaction C 2 Me C 2 Me H 2 CPA (10 mol%) Solvent, T 1a 2a 3aa Entry CPA T Solvent Yield (%) Ee (%) 8 ()-C8 rt CCl 4 92 <5 9 ()-C9 rt CCl (S)-C10 rt CCl (S)-C3 rt DCM (S)-C3 rt Toluene (S)-C3 rt Cyclohexane (S)-C3 rt MeH (S)-C3 0 CCl a (S)-C3 0 CCl b (S)-C3 0 CCl b (S)-C3 0 CCl 4 /Cyclohexane (1:4) a MgS 4 (100 mg) was added, b MgS 4 (100 mg) and Fe(Tf) 3 (10 mol%) was added.
10 Substrate Scope H 2 (S)-C3 (10 mol%) Fe(Tf)3 (10 mol%) CCl 4/Cyclohexane (1:4) MgS4, 0 o C 1a-1h 2a 3aa-3ha C 2 Me C 2 Me C 2 Me C 2 Me Cl F 3aa 4.0 d, 96% ee (95%) 3ba 4.0 d, 95% ee (93%) 3ca 3.5 d, 95% ee (91%) 3da 4.0 d, 90% ee (93%) C 2 Me C 2 Me C 2 Me C 2 Me Me Cl Cl F Cl F CF 3 3ea 4.0 d, 86% ee (91%) 3fa 4.0 d, 94% ee (94%) 3ga 4.0 d, 95% ee (92%) 3ha 3.5 d, 97% ee (93%)
11 Substrate Scope H 2 (S)-C3 (10 mol%) Fe(Tf)3 (10 mol%) CCl 4/Cyclohexane (1:4) MgS4, 0 o C 1i-1n 2a 3ia-3na C 2 Me C 2 Me C 2 Et S 3ia 4.5 d, 86% ee (86%) C 2 i Pr 3ja 4.5 d, 86% ee (93%) C 2allyl 3ka 4.0 d, 96% ee (94%) C 2 3la 4.0 d, 96% ee (92%) 3ma 4.0 d, 95% ee (90%) 3na 4.0 d, 94% ee (91%)
12 Substrate Scope C 2 Me 1a C 2 Me H 2 2a-2h (S) - C3 ( 10 mol%) Fe ( Tf)3 (10 mol%) CCl 4 /Cyclohexane ( 1:4) MgS 4, 0 o C 3aa-3ah C 2 Me C 2 Me C 2 Me C 2 Me H 3aa 4.0 d, 96% ee ( 95%) 3ab 4.0 d, 94% ee ( 95%) 2 3ac 4.0 d, 98% ee ( 83%) Ph 3ad 4.0 d, 96% ee ( 95%) C 2 Me C 2 Me C 2 Me C 2 Me Ph Ph Cl Me 3ae 4.0 d, 85% ee ( 94%) Me 3af 4.0 d, 88% ee ( 86%) 3ag 4.0 d, 90% ee ( 95%) 3ah 4.0 d, 86% ee ( 94%)
13 Synthetic Application C 2 Me C 2 Me H 2 (S) - C3 ( 10 mol%) Fe ( Tf)3 (10 mol%) CCl 4 /Cyclohexane ( 1:4) MgS 4, 0 o C 1a 2a 3aa (3.2 mmol, 1.01 g) 92% yield, 95% ee C 2 Me C 2 Me H 2 PPh 2 (S) - C3 ( 10 mol%) Fe ( Tf)3 (10 mol%) 1a Cl 2i CCl 4 /Cyclohexane ( 1:4) MgS 4, 0 o C, 5 d PPh 2 Cl 3ai 41% yield, 88% ee
14 Generality of the Solvent-Dependence C 2 Me C 2 Me H 2 (S)-C3 (10 mol%) Fe(Tf)3 (10 mol%) CCl 4 /EtH (1:3), rt 1 2a 3 Entry a (S)-3 Yield (%) b Ee (%) c 1 3--C 6 H 4 3aa Cl-C 6 H 4 3ba F-C 6 H 4 3ca naphthyl 3ia thienyl 3ja a 1 (0.15 mmol), 2a (0.1 mmol), (S)-C3 (0.01 mmol) and Fe(Tf) 3 (0.01 mmol) in CCl 4 /EtH (0.5 ml/1.5 ml). b solated yield. c Determined by HPLC.
15 Proposed eaction Process C 2 Me C 2 Me H 2 CPA (10 mol%) Fe(Tf)3 (10 mol%) Solvent H 2 id -H 2 C 2 Me C 2 Me C 2 Me H id H A Key intermediate for asymmetric control B
16 Synthesis of Axially Chiral Styrenes u H u CH CH Amine (5 mol%) 24 examples up to 99% yield up to 95% ee H Amine = TPS, = 3,5-(C H 3)2C 6 H 3 Tan, B. et al. at. Commun. 2017, 8, 15238
17 Axially Chiral Styrenes 1 3 Base 1 M 3 E H 2 2 E chiral achiral racemic Axially chiral styrenes Ph Ph Ph Ph Me Et KH Me K Et Me Me Me Et Me Me Et Et Et Et Et 1 93% ee 2 66% ee 3 65% ee at -20 o C 34% ee stirred at rt for 1 h Fuji, K. et al. J. Am. Chem. Soc. 1991, 113, 9694.
18 Synthesis of Axially Chiral Styrenes u u u H H H H H Several unprecedented issues: 1) Selection of suitable nucleophiles? 2) Styrenes exist axial chirality or not? 3) How to control E/Z selectivity? 4) How to control enantioselectivity? u H 2 CH Tan, B. et al. at. Commun. 2017, 8, 15238
19 Computed otation Barriers F S CH CH Me CH CH H A B C D E Barrier t 1/2 ( 25 o C) 67.8 KJ/mol s KJ/mol 4476 days KJ/mol 5 days KJ/mol days KJ/mol 3272 days
20 ptimization of the eactions CH 10 mol% Cat. Solvent, T 1a 2a 3a CH H Cat. C1-C7 C1: = TMS, = Ph C2: = TMS, = 3,5- ( CF 3)2C 6 H 3 C3: = TMS, = 3,5- ( CH 3)2C 6 H 3 C4: = TBS, = 3,5- ( CH 3)2C 6 H 3 C5: = TPS, = 3,5- ( CH 3)2C 6 H 3 C6: = TBS, = Ph C6: = TPS, = Ph Entry a Cat. T Solvent Yield (%) b Ee (%) c 1 C1 rt CHCl C2 rt CHCl 3 trace D 3 C3 rt CHCl C4 rt CHCl C5 rt CHCl C6 rt CHCl C7 rt CHCl C5 rt DCM C5 rt toluene C5 (5 mol%) rt DCM C5 (5 mol%) 0 DCM C5 (5 mol%) -20 DCM trace D 13 d C5 (5 mol%) 0 DCM a 1a (0.05 mmol), 2a (1.1 eq.), cat. (10 mol%), solvent (0.5 ml), rt, 24 h. b solated yield. c Determined by HPLC. d Li (0.025 mmol) was added.
21 Substrate Scope or 1a C C 1b 2a-f CH 5 mol% C5 Li, DCM, 0 o C u 3a-f CH CH CH CF 3 CH S 2 Ph 3a 96% yield, 94% ee 3b 95% yield, 90% ee 3c 40% yield 82% ee ( Z/E = 96/4) CH CH CH Me 3d 99% yield, 92% ee 3e 75% yield, 87% ee 3f 99% yield, 88% ee
22 Substrate Scope or 1a C C 1b 2g-l CH 5 mol% C5 Li, DCM, 0 o C u 3g-l CH CH CH CH 3g 99% yield, 88% ee 3h 99% yield, 87% ee 3i 89% yield, 54% ee C C C C CH C CH C CH i Pr 3j 99% yield, 95% ee 3k 93% yield, 94% ee 3l 98% yield, 86% ee
23 Substrate Scope u H CH 5 mol% C5 Li, DCM, 0 o C u CH 1c- j 2a 3m-t Cl CH CH CH CH 3m 92% yield, 94% ee 3n 89% yield, 94% ee 3o 99% yield, 94% ee 3p 87% yield, 94% ee C 2 Me C 2 Et Cl CH CH CH CH 3q 49% yield, 90% ee 3r 57% yield 90% ee ( Z/E = 90/10) 3s 93% yield, 2.1:1 dr 85% ee ( ma j or ) 96% ee ( minor ) 3t 97% yield, 2.3:1 dr 86% ee ( ma j or ) 94% ee ( minor )
24 Synthetic Application CH 2 H abh 4 CuCl H C 2 H 4 67 yield, 94% ee TsH HCH 2 CH 2 H 3n 94% ee CH n BuLi 5 51 yield, 94% ee H 6 63 yield, 94% ee 7 48 yield, 94% ee H Zn CH Ph 3 PCH 3 K CF 3-10 o C CF 3 CF yield > 99/1 dr, 99% ee 3u 99% ee 9 80 yield, 99% ee
25 Summary ' H 2 CPA ( 10 mol%) '' LA ( 10 mol%) ' '' CPA 9-anthryl P H 9-anthryl Tan, B. et al. J. Am. Chem. Soc. 2017, 139, u H CH Amine ( 5 mol%) u CH H Amine = TPS, = 3,5- ( CH 3)2C 6 H 3 Tan, B. et al. at. Commun. 2017, 8,
26 The First Paragraph As one of the most prominent classes of heterocyclic compounds, pyrroles are key structural motifs in biologically active compounds and useful building blocks in the synthesis of natural products, as well as in material sciences. cordingly, their synthesis has always been among the most important research areas in synthetic chemistry and numerous methods have been widely developed. ne of the most common approaches for the construction of pyrroles is the Paal Knorr reaction in which 1,4-diketones are converted into pyrroles from the reaction with primary amine or ammonia by acid-mediated dehydrative cyclization. emarkably, this reaction was first reported in 1884; however, catalytic asymmetric Paal Knorr pyrrole synthesis still remained elusive to date.
27 The First Paragraph ne of the easily missing reasons is the absence of intrinsic chirality at the pyrrole, revealing no obvious handle for asymmetric induction. We questioned whether the formation of chiral pyrroles in the course of the reaction would be feasible. Here we report an acid-catalyzed asymmetric Paal Knorr reaction for atroposelective synthesis of axially chiral arylpyrroles
28 The Last Paragraph n summary, we have developed a general and efficient method for accessing enantiomerically pure arylpyrroles by utilizing the first catalytic asymmetric Paal Knorr reaction. A wide range of axially chiral arylpyrroles were obtained in high yields with good to excellent enantioselectivities. The combined-acid catalytic system involving a Lewis acid and a chiral phosphoric acid was the key point to improve the enantioselectivity. nterestingly, an unexpected solvent-dependent inversion of the enantioselectivity was observed. We anticipate that this strategy will be applied to natural product synthesis and the axially chiral arylpyrroles will have potential application in asymmetric catalysis.
Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet Spengler Reaction of Indolyl Dihydropyridines
Literature Report V Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet Spengler Reaction of Indolyl Dihydropyridines Reporter Checker Date : Xiao-Yong Zhai : Xin-Wei Wang : 2018-04-02 You,
Literature Report. Catalytic Enantioselective Synthesis of Isoindolinones through a Biomimetic Approach. : Zhong Yan : Ji Zhou :
Literature Report Catalytic Enantioselective Synthesis of Isoindolinones through a Biomimetic Approach Reporter Checker Date : Zhong Yan : Ji Zhou : 2017-12-22 Min, C.; Lin, Y.; Seidel, D. Angew. Chem.
Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02
![Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02](/thumbs/93/114018431.jpg "Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02")
Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02 Xiao, W.-J. et al. J. Am. Chem. Soc. 2016, 138, 8360.
Enantioselective 1,1-Arylborylation of. Transfer with Pd Catalysis
Enantioselective 1,1-Arylborylation of Alkenes: Merging Chiral Anion Phase Transfer with Pd Catalysis Reporter: Lian-Jin Liu Checker: Wen-Xue Huang Date: 12/05/2015 F. Dean Toste University of California,
Palladium-Catalyzed Asymmetric Benzylic Alkylation Reactions
Palladium-Catalyzed Asymmetric Benzylic Alkylation Reactions Reporter: Hong-Qiang Shen Checker: Cong Liu Date: 2016/07/12 Masahiro Miura et al. Angew. Chem. Int. Ed. 2016, 55, 6973. Masahiro Miura Osaka
Synthetic Methodology. Using Tertiary Phosphines. as Nucleophilic Catalysts
Synthetic Methodology Using Tertiary osphines as Nucleophilic Catalysts 1 3 2 u 2 (P 3 ) 3 4 1 2 D. Ma, X. Lu 1988 1 2 Pd 2 (dba) 3.CCl 3 /P 3 /Ac or Pd(Ac) 2 /P 3 1 2 B. M. Trost 1988 1 3 2 u 2 (P 3 )
Asymmetric Nucleophilic Catalysis
Asymmetric ucleophilic Catalysis Chiral catalyst X 2 Chiral catalyst X = alkyl, X 1 2 1 Vedejs, E.; Daugulis,. J. Am. Chem. Soc. 2003, 125, 4166-4173 Shaw, S. A.; Aleman,.; Vedejs, E. J. Am. Chem. Soc.
Chiral Brønsted Acid Catalysis
Chiral Brønsted Acid Catalysis Aryl Aryl Aryl Aryl S CF 3 2 P Fe CF 3 CF 3 2 Jack Liu ov. 16, 2004 CF 3 Introduction Chiral Brønsted acid catalysis in nature: enzymes and peptides Chiral Brønsted acid
Literature Report IX. Cho, S. H. et al. Org. Lett. 2016, 18, Cho, S. H. et al. Angew. Chem. Int. Ed. 2017, 56,
Literature Report IX ynthesis of β-aminoboronates by Copper(I)- Catalyzed Addition of Diborylalkanes to Imines Reporter Checker Date : hubo Hu : Xiaoyong Zhai : 2017-9-1818 Cho,. H. et al. rg. Lett. 2016,
Supporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information for Chiral Brönsted Acid Catalyzed Asymmetric Baeyer-Villiger Reaction of 3-Substituted Cyclobutanones Using Aqueous
Zr-Catalyzed Carbometallation
-Catalyzed Carbometallation C C C C ML n C C ML n ML n C C C C ML n ML n C C ML n Wipf Group esearch Topic Seminar Juan Arredondo November 13, 2004 Juan Arredondo @ Wipf Group 1 11/14/2004 Carbometallation
Chiral Bronsted Acids as Catalysts
Chiral Bronsted Acids as Catalysts Short Literature Seminar 6/3/08 Dustin aup BIL Derived osphoric Acids - First reported in 1992 as a ligand by irrung and coworkers. 4 h 2 irrung Tet. Lett. 1992, 33,
Supporting Information
Supporting Information Enantioselective Synthesis of 3-Alkynyl-3-Hydroxyindolin-2-ones by Copper-Catalyzed Asymmetric Addition of Terminal Alkynes to Isatins Ning Xu, Da-Wei Gu, Jing Zi, Xin-Yan Wu, and
Supporting Information-II. Asymmetric Synthesis of Drug-like Spiro[chroman-3,3'- indolin]-2'-ones through Aminal-catalysis
![Supporting Information-II. Asymmetric Synthesis of Drug-like Spiro[chroman-3,3'- indolin]-2'-ones through Aminal-catalysis](/thumbs/88/115806705.jpg "Supporting Information-II. Asymmetric Synthesis of Drug-like Spiro[chroman-3,3'- indolin]-2'-ones through Aminal-catalysis")
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information-II Asymmetric Synthesis of Drug-like Spiro[chroman-3,3'- indolin]-2'-ones through Aminal-catalysis D.
"-Amino Acids: Function and Synthesis
"-Amino Acids: Function and Synthesis # Conformations of "-Peptides # Biological Significance # Asymmetric Synthesis Sean Brown MacMillan Group eting ovember 14, 2001 Lead eferences: Cheng,. P.; Gellman,
Functionalization of C(sp 3 ) H Bonds Using a Transient Directing Group
Literature eport Functionalization of C(sp 3 ) Bonds Using a Transient Directing Group eporter: Mu-Wang Chen Checker: Yue Ji Date: 2016-04-05 Yu, J.-Q. et al. Science 2016, 351, 252-256. Scripps esearch
Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization
![Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization](/thumbs/82/85235286.jpg "Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization")
Total Synthesis of (+/-)-Goniomitine via a Formal itrile/donor-acceptor Cyclopropane [3 + 2] Cyclization (-)-Goniomitine Christian L. Morales and Brian Pagenkopf* rganic Letters, ASAP Current Literature
Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-
Literature Report Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)- aseseazines A and B Reporter: Mu-Wang Chen Checker: Zhang-Pei Chen Date: 2013-05-28 Reisman,
Literature Report 1. Total Syntheses of Disorazoles A1 and B1 and Full Structural Elucidation of Disorazole B1
Literature Report 1 Total Syntheses of Disorazoles A1 and B1 and Full Structural Elucidation of Disorazole B1 Reporter: Kui Liu Checker: Xiao-Yong Zhai Date: 2018-05-28 Nicolaou K C *; Bellavance G ; Buchman
Journal Club Presentation by Remond Moningka 04/17/2006
β-alkyl-α-allylation of Michael Acceptors through the Palladium-Catalyzed Three-Component Coupling between Allylic Substrate, Trialkylboranes, and Activated lefins Yoshinori Yamamoto, et al. J. rg. Chem.
Stereoselective Synthesis of Configurationally Stable Functionalized Ethano-Bridged Tröger Bases
Stereoselective Synthesis of Configurationally Stable Functionalized Ethano-Bridged Tröger Bases Michon, C.; Sharma, A.; Bernardinelli, G.; Francotte, E.; Lacour, J. Chem. Commun., 2010, 46, 2206-2208
i-pr 2 Zn CHO N Sato, I.; Sugie, R.; Matsueda, Y.; Furumura, Y.; Soai, K. Angew. Chem., Int. Ed. Engl. 2004, 43, 4490
Asymmetric Synthesis Utilizing Circularly Polarized Light Mediated by the otoequilibration of Chiral lefins in Conjuction with Asymmetric Autocatalysis l-cpl r-cpl (S) () Sato, I.; Sugie,.; Matsueda, Y.;
Chem 253 Problem Set 7 Due: Friday, December 3, 2004
Chem 253 roblem Set 7 ue: Friday, ecember 3, 2004 Name TF. Starting with the provided starting material, provide a concise synthesis of. You may use any other reagents for your synthesis. It can be assumed
Literature Report 3. Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A. Date :
Literature Report 3 Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A Reporter : Xiao-Yong Zhai Checker : Shubo u Date : 2017-10-30 Pritchett, B. P.; Donckele, E. J.; Stoltz, B. M. Angew.
Development of Chiral Phosphine Olefin Ligands and Their Use in Asymmetric Catalysis
Development of Chiral osphine lefin Ligands and Their Use in Asymmetric Catalysis 2 Wei-Liang Duan July 31, 2007 Research Works in Hayashi Group, Kyoto University (ct, 2003 Mar, 2007) Conventional Chiral
Literature Report III
Literature Report III Regioselective ydroarylation of Alkynes Reporter: Zheng Gu Checker: Cong Liu Date: 2017-08-28 Cruz, F. A.; Zhu, Y.; Tercenio, Q. D.; Shen, Z.; Dong, V. M. J. Am. Chem. Soc. 2017,
Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition
ASYMMETRIC PALLADIUM-CATALYZED ALKENE CARBOAMINATION REACTIONS FOR THE SYNTHESIS OF CYCLIC SULFAMIDES
AYMMETIC PALLADIUM-CATALYZED ALKEE CABAMIATI EACTI F TE YTEI F CYCLIC ULFAMIDE Chem. Eur. J. 2016, 22, 5919 5922 Zachary J. Garlets, Kaia. Parenti, and John P. Wolfe James Johnson Wipf Group Current Literature
Direct Organocatalytic Enantioselective Mannich Reactions of Ketimines: An Approach to Optically Active Quaternary α-amino Acid Derivatives
Direct rganocatalytic Enantioselective Mannich eactions of Ketimines: An Approach to ptically Active Quaternary α-amino Acid Derivatives Wei Zhang, Steen Saaby, and Karl Anker Jorgensen The Danish ational
Stereoselective reactions of the carbonyl group
1 Stereoselective reactions of the carbonyl group We have seen many examples of substrate control in nucleophilic addition to the carbonyl group (Felkin-Ahn & chelation control) If molecule does not contain
Homogeneous Catalysis - B. List
omogeneous Catalysis - B. List 2.2.2 Research Area "rganocatalytic Asymmetric α-alkylation of Aldehydes" (B. List) Involved:. Vignola, A. Majeed Seayad bjective: α-alkylations of carbonyl compounds are
Rhodium-Catalyzed Enantioselective
Rhodium-Catalyzed Enantioselective Isomerization of Oxabicycles Reporter: Jie Wang Checker: Shubo Hu Date: 2017-07-03 Yen, A.; Choo, K.-L.; Yazdi, S. K.; Franke, P. T.; Webster, R.; Franzoni, I.; Loh,
Short Access to (+)-Lupinine and (+)-Epiquinamide via Double Hydroformylation
Short Access to (+)-Lupinine and (+)-Epiquinamide via Double Hydroformylation Kai Gao Checker: Changbin Yu Mann, A.* et al rg. Lett. 2009, ASAP Strategy for the formation of quinolizidine alkaloids R H
Catalytic alkylation of remote C H bonds enabled by proton-coupled electron transfer
Catalytic alkylation of remote C bonds enabled by proton-coupled electron transfer Reporter: Ji Zhou Checker: Shubo u Date: 2016/11/14 Choi, G. J.; Zhu, Q.-L.; Miller, D. C.; Gu, C. J.; Knowles, R. R.
Measuring enzyme (enantio)selectivity
Measuring enzyme (enantio)selectivity Types of selectivity - review stereoisomers Stereoselective synthesis (create) vs. resolutions (separate) Enantioselectivity & enantiomeric purity Ways to measure
Electrophilic Carbenes
Electrophilic Carbenes The reaction of so-called stabilized diazo compounds with late transition metals produces a metal carbene intermediate that is electrophilic. The most common catalysts are Cu(I)
Supporting Information:
Supporting Information: An rganocatalytic Asymmetric Sequential Allylic Alkylation/Cyclization of Morita-Baylis-Hillman Carbonates and 3-Hydroxyoxindoles Qi-Lin Wang a,b, Lin Peng a, Fei-Ying Wang a, Ming-Liang
Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from N-tert- Butanesulfinyl Aldimines
Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from -tert- Butanesulfinyl Aldimines R BR 2 J. Am. Chem. Soc. 2008, 130, 6910. Melissa A. Beenen, Chihul An, and Jonathan A. Ellman rrent
Literature Report I. Total Synthesis of (+)-Piperarborenine B. Reporter: Zheng Gu. Date:
Literature Report I Total Synthesis of (+)-Piperarborenine B Reporter: Zheng Gu Checker: Bo Song Date: 2016-12-12 Hu, J. L.; Xie, Z. W.; Tang, Y. J. Am. Chem. Soc. 2016, 138, 13151. Panish, R. A.; Chintala,
Asymmetric Catalysis by Lewis Acids and Amines
Asymmetric Catalysis by Lewis Acids and Amines Asymmetric Lewis acid catalysis - Chiral (bisooxazoline) copper (II) complexes - Monodentate Lewis acids: the formyl -bond Amine catalysed reactions Asymmetric
Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis
Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis C 3 C3 Liffert, R., Linden, A., Gademann, K. J. Am. Chem. Soc. 2017, 139, 16096 Presented by: Brendyn Smith CEM 852
Supporting Information. Rh(III)-Catalyzed C7-Thiolation and Selenation of Indolines
Supporting Information Rh(III)-Catalyzed C7-Thiolation and Selenation of Indolines Wucheng Xie, Bin Li, Baiquan Wang *,,, State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center
Highlights of Schmidt Reaction in the Last Ten Years
ighlights of Schmidt eaction in the Last Ten Years Dendrobates histrionicus Jack Liu ov. 18, 2003 Introduction Classical Schmidt reaction of aldehydes and carboxylic acids Classical Schmidt reaction of
Supporting Information For. Visible Light Photocatalytic Radical-Radical Cross-Coupling. Reactions of Amines and Carbonyls: A Route to 1,2-Amino
Supporting Information For Visible Light Photocatalytic Radical-Radical Cross-Coupling Reactions of Amines and Carbonyls: A Route to,2-amino Alcohols Wei Ding, Liang-Qiu Lu, Jing Liu, Dan Liu, Hai-Tao
Lewis Base Catalysis: the Aldol Reaction (Scott Denmark) Tom Blaisdell Friday, January 17 th 2014 Topic Talk
Lewis Base Catalysis: the Aldol eaction (Scott Denmark) Tom Blaisdell Friday, January 17 th 2014 Topic Talk Scott E. Denmark 1975 - S.B. in Chemistry MIT (ichard. olm and Daniel S. Kemp) 1980 - D.Sc in
Organic Tutorials 3 rd Year Michaelmas Transition Metals in Organic Synthesis: (General paper level) ! 1! Reading
rganic Tutorials 3 rd Year Michaelmas 2010 Transition Metals in rganic Synthesis: (General paper level) Reading 1. Lecture Course, and suggested references from this. 2. Clayden, Greaves, Warren and Wothers.
Molybdenum-Catalyzed Asymmetric Allylic Alkylation
Molybdenum-Catalyzed Asymmetric Allylic Alkylation X MoL n u u * Tommy Bui 9/14/04 Asymmetric Allylic Alkylation from a Synthetic Viewpoint X X M u u * and/or u form a C-C bond with the creation of a new
Chiral Proton Catalysis in Organic Synthesis. Samantha M. Frawley Organic Seminar September 14 th, 2005
Chiral Proton Catalysis in rganic Synthesis Samantha M. Frawley rganic Seminar September 14 th, 2005 Seminar utline Introduction Lewis Acid-assisted Chiral Brønsted Acids Enantioselective protonation for
Keisuke Suzuki. Baran lab Group Meeting 6/11/16. Shigenobu Umemiya. Akira Suzuki. Takanori Suzuki (Hokkaido University)
197.D., Teruaki Mukaiyama, University of Tokyo 193 Assistant Professor, Keio University 197 Lecturer, Keio University 199 Assocate Professor, Keio University 1990 Visiting Professor, ET 1994 ull Professor,
Additions to Metal-Alkene and -Alkyne Complexes
Additions to tal-alkene and -Alkyne Complexes ecal that alkenes, alkynes and other π-systems can be excellent ligands for transition metals. As a consequence of this binding, the nature of the π-system
Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones
Asymmetric Organocatalytic Strecker-Type Reactions of Aliphatic N,N- Dialkylhydrazones Aurora Martínez-Muñoz, David Monge,* Eloísa Martín-Zamora, Eugenia Marqués-López, Eleuterio Álvarez, Rosario Fernández,*
Supporting Information
Supporting Information Cobalt(II)-Catalyzed Acyloxylation of C- Bonds in Aromatic Amides with Carboxylic Acids Rina Ueno, Satoko atsui, and aoto Chatani* Department of Applied Chemistry, Faculty of Engineering,
Short Literature Presentation 10/4/2010 Erika A. Crane
Copper-Catalyzed Enantioselective Synthesis of trans-1- Alkyl-2-substituted Cyclopropanes via Tandem Conjugate Additions-Intramolecular Enolate Trapping artog, T. D.; Rudolph, A.; Macia B.; Minnaard, A.
a-aminoallylation of Aldehydes with Ammonia: Stereoselective Synthesis of Homoallylic Primary Amines
a-aminoallylation of Aldehydes with Ammonia: Stereoselective Synthesis of omoallylic Primary Amines 1 3 2 3 ML n 1 2 2 3 Masaharu Sugiura, Keiichi irano and Shu Kobayashi JACS ASAP ryan Wakefield @ Wipf
Strategies for Catalytic Asymmetric Electrophilic a Halogenation of Carbonyl Compounds
Strategies for Catalytic Asymmetric Electrophilic a alogenation of Carbonyl Compounds 1 2 Y Catalyst [X + ] 1 X! 2 Y intermann, L. ; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359 4362 amashima, Y.; Sodeoka,
Asymmetric Radical Reactions. Zhen Liu 08/30/2018
Asymmetric adical eactions Zhen Liu 08/30/2018 Contents Introduction eactions Using Chiral Auxiliary Chiral Lewis Acid-diated eactions Transition tal-catalyzed eactions eactions Using Chiral rganocatalysts
Racemic catalysis through asymmetric activation*
Pure Appl. Chem., Vol. 73, No. 2, pp. 255 259, 2001. 2001 IUPAC Racemic catalysis through asymmetric activation* Koichi Mikami, Toshinobu Korenaga, Yousuke Matsumoto, Makoto Ueki, Masahiro Terada, and
Kinetic Resolutions. Some definitions and examples Resolution: A process leading to the separation of enantiomers, or derivatives thereof.
Material outline: For the Scientist in you: Definitions Theoretical treatment Kinetic esolutions General eferences: Vedejs, ACIEE, 2005, 3974 Jacobsen, Adv. Syn. Cat. 2001, 5 Kagan, Topics in Stereochemistry,
Supporting Information. Two Catalytic Methods of an Asymmetric Wittig [2,3]-Rearrangement
![Supporting Information. Two Catalytic Methods of an Asymmetric Wittig [2,3]-Rearrangement](/thumbs/94/118789403.jpg "Supporting Information. Two Catalytic Methods of an Asymmetric Wittig [2,3]-Rearrangement")
Supporting Information Two Catalytic Methods of an Asymmetric Wittig [2,3]-Rearrangement Maksim Ošeka, Mariliis Kimm, Ivar Järving, Kristin Lippur, and Tõnis Kanger * Department of Chemistry, Tallinn University
Chiral Catalyst II. Palladium Catalysed Allylic Displacement ( -allyl complexes) 1. L n Pd(0) 2. Nuc
Chiral Catalyst II ast lecture we looked at asymmetric catalysis for oxidation and reduction Many other organic transformations, this has led to much investigation Today we will look at some others...
Studies on Heck and Suzuki Reactions Catalyzed by Palladium(0) and Wacker- Type Oxidative Cyclization Catalyzed by Palladium(II)
Studies on eck and Suzuki Reactions Catalyzed by Palladium(0) and Wacker- Type xidative Cyclization Catalyzed by Palladium() Zuhui Zhang enmark Group Meeting 10/21/2008 1 Part ne: Palladium(0)-Catalyzed
A Stereoselective Synthesis of (+)-Gonyautoxin 3
A Stereoselective Synthesis of (+)-Gonyautoxin 3 Mulcahy, J. V.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 12630-12631 Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via
A New Model for Asymmetric Amplification in Amino Acid Catalysis - Supporting information
A New Model for Asymmetric Amplification in Amino Acid Catalysis - Supporting information Martin Klussmann, Hiroshi Iwamura, Suju P. Mathew, David H. Wells, Urvish Pandya, Alan Armstrong and Donna G. Blackmond
Palladium-Catalyzed Asymmetric [3+2] Cycloaddition to Construct 1,3-Indandione and Oxindole-Fused Spiropyrazolidine Scaffolds
![Palladium-Catalyzed Asymmetric [3+2] Cycloaddition to Construct 1,3-Indandione and Oxindole-Fused Spiropyrazolidine Scaffolds](/thumbs/86/93510386.jpg "Palladium-Catalyzed Asymmetric [3+2] Cycloaddition to Construct 1,3-Indandione and Oxindole-Fused Spiropyrazolidine Scaffolds")
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supporting Information Palladium-Catalyzed Asymmetric [3+2] Cycloaddition to Construct 1,3-Indandione
Asymmetric Autocatalysis Triggered by Carbon Isotope ( 13 C/ 12 C) Chirality
Asymmetric Autocatalysis Triggered by Carbon Isotope ( 13 C/ 12 C) Chirality Hong Ren 06-19-09 Asymmetric Autocatalysis Triggered by Carbon Isotope ( 13 C/ 12 C) Chirality Hong Ren 06-19-09 Asymmetric
Chiral Diol Promoted Boronates Addi3on Reac3ons. Lu Yan Morken Group Boston College
Chiral Diol Promoted Boronates Addi3on Reac3ons Lu Yan Morken Group Boston College Main Idea R R B or R R B Ar * exchange B * * or B Ar R 1 R 1 R 2 R 1 R 2 Products not nucleophilic enough nucleophilic
个人简介 : 工作及教育经历 : 研究方向 : 主持及参加的科研项目 :
个人简介 : 1977.05 022-83955358 13622110642 Primer673@126.com; sukunmei@tjpu.edu.cn 工作及教育经历 : 2012/11 天津工业大学化学与化工学院教授 2009/09 2015/10 天津工业大学化学与化工学院副教授 2007/09 2009/10 天津工业大学化学与化工学院讲师 2003/09 2007/06 中国科学院植物研究所博士研究生
Shi Asymmetric Epoxidation
Shi Asymmetric Epoxidation Chiral dioxirane strategy: R 3 + 1 xone, ph 10.5, K 2 C 3, H 2, C R 3 formed in situ catalyst (10-20 mol%) is prepared from D-fructose, and its enantiomer from L-sorbose oxone,
Chiral Ionic Liquids (CILs) in Asymmetric Synthesis: The story so far.
Chiral Ionic Liquids (CILs) in Asymmetric Synthesis: The story so far. Literature Presentation Aman Desai 06.16.06 1. Angew. Chem. Int. Ed. 2006, 45, 3689 2. Angew. Chem. Int. Ed. 2006, 45, 3093 3. Tetrahedron:
Copper-Catalyzed Reaction of Alkyl Halides with Cyclopentadienylmagnesium Reagent
Copper-Catalyzed eaction of Alkyl Halides with Cyclopentadienylmagnesium eagent Mg 1) cat. Cu(Tf) 2 i Pr 2, 25 o C, 3 h 2) H 2, Pt 2 Masahiro Sai, Hidenori Someya, Hideki Yorimitsu, and Koichiro shima
Nickel-Catalyzed Reductive Cross-Electrophile-Coupling Between Aryl and Alkyl Halides
ickel-catalyzed Reductive Cross-Electrophile-Coupling Between Aryl and Alkyl Halides Eunjae Shim Zakarian Group Literature Talk / Dec 13 th, 2018 University of California, Santa Barbara Table of Contents
Metal-catalyzed asymmetric hetero-diels-alder reactions of unactivated dienes with glyoxylates
Pure & Appl. Chern., Vol. 70, No. 5, pp. 11 17-1 122, 1998. Printed in Great Britain. (0 1998 IUPAC Metal-catalyzed asymmetric hetero-diels-alder reactions of unactivated dienes with glyoxylates Mogens
Strategies for Stereocontrolled Synthesis
Chemistry. Synthetic rganic Chemistry II Lecture 3 March, 2007 Rick L. Danheiser Massachusetts Institute of Technology! Thermodynamic Control Strategies! Kinetic Control Strategies! Strategies for the
Asymmetric Lewis Base Strategies for Heterocycle Synthesis
Asymmetric Lewis Base trategies for eterocycle ynthesis Dr Andrew mith EatCEM, chool of Chemistry, University of t Andrews 1st cottish-japanese ymposium of rganic Chemistry, University of Glasgow Friday
Supporting information
Supporting information Asymmetric [3+2] Annulation of Allenes with Maleimides Catalyzed by Dipeptide-Derived Phosphines: Facile Creation of Functionalized Bicyclic Cyclopentenes Containing two Tertiary
The aldol reaction with metal enolates proceeds by a chair-like, pericyclic process: favored. disfavored. favored. disfavored
The aldol reaction with metal enolates proceeds by a chair-like, pericyclic process: Z-enolates: M 2 M 2 syn 2 C 2 favored 2 M 2 anti disfavored E-enolates: M 2 2 C 3 C 3 C 2 favored 2 M M disfavored In
TMSCl imidazole DMF. Ph Ph OTMS. Michael reaction. Michael reaction Ph R 3. epoxidation O R
eaction using diarylprolinol silyl ether derivatives as catalyst 1) C Et K C 3, ) MgBr, TF TMS hexane, 0 o C TBS p- C 6 4, T C Et 85%, 99% ee Angew. Chem., nt. Ed., 44, 41 (005). rg. Synth., 017, 94, 5.
Wilkinson s other (ruthenium) catalyst
Wilkinson s other (ruthenium) catalyst Cl 3 ; 2 h 3, reflux 3h h 3 Cl h 3 h Cl 3 Good catalyst especially for 2 1-alkenes 2, base toluene Cl h 3 h 3 h 3 Et 3 Cl h 3 Cl h 3 h 3 R h 3 h 3 Cl h 3 R RC 2 C
Stereodivergent Catalysis. Aragorn Laverny SED Group Meeting July
Stereodivergent Catalysis Aragorn Laverny SED Group Meeting July 31 2018 1 Stereodivergent Catalysis In the context of asymmetric synthesis, a stereodivergent process is one that allows access to any given
Stable gold(iii) catalysts by oxidative addition of a carboncarbon
Stable gold(iii) catalysts by oxidative addition of a carboncarbon bond Chung-Yeh Wu, Takahiro oribe, Christian Borch Jacobsen & F. Dean Toste ature, 517, 449-454 (2015) presented by Ian Crouch Literature
Literature Report. A 11-Steps Total Synthesis of Magellanine through a Gold(І)-Catalyzed Dehydro Diels-Alder Reaction
Literature Report 11-Steps Total Synthesis of Magellanine through a Gold(І)-Catalyzed ehydro iels-lder Reaction Reporter: ong-qiang Shen Checker: Cong Liu ate: 2017/06/19 McGee, P.; Bétournay, G.; Barabé,
Copper-Catalyzed Oxidative Amination of Benzoxazoles via C-H and C-N Bond Activation: A
Supporting Information for: Copper-Catalyzed xidative Amination of Benzoxazoles via C-H and C- Bond Activation: A ew Strategy for Using Tertiary Amines as itrogen Group Sources Shengmei Guo, Bo Qian, Yinjun
Table of Contents 1. General procedure for the chiral phosphoric acid catalyzed asymmetric reductive amination using benzothiazoline
Enantioselective Organocatalytic Reductive Amination of Aliphatic Ketones by Benzothiazoline as Hydrogen Donor Kodai Saito, Takahiko Akiyama* Department of Chemistry, Faculty of Science, Gakushuin University,
Use of Cp 2 TiCl in Synthesis
Use of 2 TiCl in Synthesis eagent Control of adical eactions Jeff Kallemeyn May 21, 2002 eactions of 2 TiCl 1. Pinacol Coupling H H H 2. Epoxide pening H H E H Chemoselectivity Activated aldehydes (aromatic,
MODULE CODE: CHEM10003 ORGANIC CHEMISTRY 4 EXAM
School of Science and Sport Physical Sciences, Chemistry Paisley Campus Session 2014-15 Trimester 2 MDULE CDE: CHEM10003 RGANIC CHEMISTRY 4 EXAM Date: 15th May 2015 Time: 10.00am 12.00pm Attempt THREE
A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones and Aldehydes
A ighly Efficient rganocatalyst for Direct Aldol Reactions of Ketones and Aldehydes Zhuo Tang, Zhi-ua Yang, Xiao-ua Chen, Lin-Feng Cun, Ai-Qiao Mi, Yao-Zhong Jiang, and Liu-Zhu Gong Contribution from the
Supporting Information
Supporting Information Construction of Highly Functional α-amino itriles via a ovel Multicomponent Tandem rganocatalytic Reaction: a Facile Access to α-methylene γ-lactams Feng Pan, Jian-Ming Chen, Zhe
Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes
Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi
Suggested solutions for Chapter 41
s for Chapter 41 41 PBLEM 1 Explain how this synthesis of amino acids, starting with natural proline, works. Explain the stereoselectivity of each step after the first. C 2 C 2 3 CF 3 C 2 2 Pd 2 C 2 +
Singapore, #05 01, 28 Medical Drive, Singapore. PR China,
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2017 Catalyst controlled Regioselectivity in Phosphine Catalysis: Synthesis of Spirocyclic Benzofuranones
Chapter 4 Electrophilic Addition to Carbon Carbon Multiple Bonds 1. Addition of H X 2. Addition of H OH and addition of Y X 3. Addition to allene and
Chapter 4 Electrophilic Addition to Carbon Carbon Multiple Bonds 1. Addition of X 2. Addition of and addition of Y X 3. Addition to allene and alkyne 4. Substitution at α-carbon 5. eactions via organoborane
CHEM 345 Problem Set 07 Key
CHEM 345 Problem Set 07 Key 1.) Fill in the appropriate reaction arrow. The starting material is on the left, the product is on the right. Use. Simple Ring Size. 5 and 6 are favored. 3 is not. That s it.
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity Reporter: Cong Liu Checker: Hong-Qiang Shen Date: 2017/02/27
When something goes wrong. Goya: Mother showing her derformed child to two women Louvre, Paris
1 ew Catalytic Asymmestric eactions Karl Anker Jørgensen Danish ational eserach Foundation: Center for Catalysis Department of Chemistry, Aarhus University Denmark kaj@chem.au.dk When something goes wrong
Denmark s Base Catalyzed Aldol/Allylation
Denmark s Base Catalyzed Aldol/Allylation Evans Group Seminar ovember 1th, 003 Jimmy Wu Lead eferences: Denmark, S. E. Acc. Chem. es., 000, 33, 43 Denmark, S. E. Chem. Comm. 003, 167 Denmark, S. E. Chem.
R 2 R 4 Ln catalyst. This manuscript describes the methods for the synthesis and application of group 4 metallocene bis(trimethylsilyl)acetylene
VII Abstracts 2011 p1 2.12.15 rganometallic Complexes of Scandium, Yttrium, and the Lanthanides P. Dissanayake, D. J. Averill, and M. J. Allen This manuscript is an update to the existing Science of Synthesis
Chapter 14. Principles of Catalysis
Organometallics Study Meeting 2011/08/28 Kimura Chapter 14. Principles of Catalysis 14. 1. General Principles 14.1.1. Definition of a Catalyst 14.1.2. Energetics of Catalysis 14.1.3. Reaction Coordinate
Supplementary Information
Catalytically Efficient Palladium anoparticles Stabilized by Click rrocenyl Dendrimers Cátia rnelas, Lionel Salmon, Jaime Ruiz Aranzaes, Didier Astruc Supplementary Information Cyclic Voltammetry (CV),
Development of Small Organic Molecules as Catalysts for Asymmetric
Development of Small Organic Molecules as Catalysts for Asymmetric Organic Transformations The development of new and efficient catalysts capable of catalyzing enantioselective transformation in a controlled
guanidine bisurea bifunctional organocatalyst
Supporting Information for Asymmetric -amination of -keto esters using a guanidine bisurea bifunctional organocatalyst Minami Odagi* 1, Yoshiharu Yamamoto 1 and Kazuo Nagasawa* 1 Address: 1 Department