Palladium-Catalyzed Asymmetric Benzylic Alkylation Reactions
|
|
|
- Philip Parker
- 6 years ago
- Views:
Transcription
1 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, Masahiro Miura Osaka University
2 Contents Introduction Asymmetric Benzylic Alkylation with Primary Benzylic Phosphates Asymmetric Benzylic Alkylation with Secondary Benzylic Carbonates Summary
3 Introduction Prof. Masahiro Miura Education: 1978 B. A. Osaka University Faculty of Engineering 1983 Ph. D. Osaka University Graduate School Humboldt Fellow with Prof. K. Griesbaum, Karlsruhe University Associate Professor, Osaka University (Japan) Professor, Osaka University (Japan)
4 Introduction Ionization of the electrophile can be challenging since the π-benzyl intermediate is dearomatized. Trost, B. M. et al. Angew. Chem. Int. Ed. 2014, 53, 2826.
5 Introduction As for Electrophiles containing a naphthalene or heteroaromatic moiety, the barrier to ionization and dearomatization is lower. Trost, B. M. et al. J. Am. Chem. Soc. 2012, 134, 5778.
6 Initial Experiment Trost, B. M. et al. J. Am. Chem. Soc. 2012, 134, 5778.
7 Optimization Experiments Entry Cs 2 CO 3 (equiv) Solvent T ( o C) Yield (%) a Ee (%) b 1 0 Toluene Toluene DCM DCM c 0.6 DCM d 0.6 DCM Reaction conditions: 4a (0.2 mmol), 2 (1.0 equiv), (η 3 -C 3 H 5 )PdCp (5.0 mol%), L1 (6.0 mol%), t BuOH (5.0 equiv), 20 h. a Isolated yield. b Determined by chiral HPLC. c 2 (1.5 equiv). d Reaction run without t BuOH.
8 Electron-Rich Phosphates
9 Optimization of Electron-Neutral Phosphates
10 Optimization of Electron-Neutral Phosphates Entry L Solvent T ( o C) Yield (%) a Ee (%) b 1 L1 DCM c 2 L2 DCM c 3 L3 DCM L4 DCM Reaction conditions: 5a (0.2 mmol), 2 (1.5 equiv), (η 3 -C 3 H 5 )PdCp (5.0 mol%),l (6.0 mol%), TEA (1.2 equiv), t BuOH (5.0 equiv), 16 h. a Isolated yield. b Determined by chiral HPLC. c Reaction run with (S,S)-L.
11 Optimization of Electron-Neutral Phosphates
12 Optimization of Electron-Neutral Phosphates Entry Solvent T ( o C) Yield (%) a Ee (%) b 1 DCM e 2 Toluene DME THF Dioxane Dioxane c Dioxane c,d Dioxane Reaction conditions: 5a (0.2 mmol), 2 (1.5 equiv), (η 3 -C 3 H 5 )PdCp (5.0 mol%),l (6.0 mol%), TEA (1.2 equiv), t BuOH (5.0 equiv), Solvent (0.5 ml),16 h. a Isolated yield. b Determined by HPLC. c Solvent (0.3 ml), d Reaction run without t BuOH, e Reaction run with (S,S)-L1.
13 Electron-Neutral Phosphates
14 Ligand Screening Miura, M. et al. Angew. Chem. Int. Ed. 2016, 55, 6973.
15 Optimization Experiments Entry Solvent Temp ( o C) Yield a (%) Ee b (%) 1 MeCN DMSO MeCN 60 (4) n.d. 4 DMSO 60 (9) n.d. 5 c MeCN c DMSO Reaction conditions: 1a (0.25 mmol), 2a (0.30 mmol), (η 3 -C 3 H 5 )PdCp (2.5 mol%), Ligand (2.5 mol%), Solvent (3.0 ml), 3-24 h. a Isolated yields are shown, yields estimated by GC are in parenthese. b Determined by chiral HPLC, n.d. = not determined. c (η 3 -C 3 H 5 )PdCp (5.0 mol%), Ligand (5.0 mol%).
16 Optimization Experiments Entry Solvent Temp ( o C) Yield a (%) Ee b (%) 1 MeCN DMSO MeCN 60 (13) n.d. 4 DMSO n.d. 5 c MeCN c DMSO Reaction conditions: 1a (0.25 mmol), 2a (0.30 mmol), (η 3 -C 3 H 5 )PdCp (2.5 mol%), Ligand (2.5 mol%), Solvent (3.0 ml), 3-24 h. a Isolated yields are shown, yields estimated by GC are in parenthese. b Determined by chiral HPLC, n.d. = not determined. c (η 3 -C 3 H 5 )PdCp (5.0 mol%), Ligand (5.0 mol%).
17 Substrate Scope
18 Substrate Scope
19 Substrate Scope
20 Plausible Mechanism
21 Control Experiments The racemization proceeds smoothly, and no enantiospecific reaction occurs. The substrate-dependent partial kinetic resolution occurs in the substitution step. Stereochemistry is controlled by the catalyst in the final C-C forming event.
22 Control Experiments
23 Naphthalene limitation
24 Naphthalene limitation
25 Naphthalene limitation
26 Summary Trost s Work: Achiral primary benzylic carbonates or phosphates Miura s Work: Racemic secondary benzyl electrophiles
27 Palladium-catalyzed cross-coupling reactions are one of the most powerful and reliable synthetic tools for the construction of versatile carbon frameworks in modern organic chemistry. Among them, the asymmetric allylic alkylation with allylic electrophiles via π-allylpalladium intermediates (Tsuji-Trost reaction) has been extensively studied and applied to the synthesis of various complex natural products and bioactive molecules. In contrast, the asymmetric benzylic alkylation with benzylic electrophiles via π-benzylpalladium intermediates has been less developed despite its isoelectronic character to the π-allylpalladium. Although related asymmetric palladium catalysis with prochiral nucleophiles and achiral primary benzylic carbonates or phosphates were recently reported by Trost and Czabaniuk, a dynamic kinetic asymmetric transformation (DYKAT) with racemic secondary benzyl electrophiles still remains largely elusive.
28 In conclusion, we have developed a Pd/(R)-H 8 -BINAP catalyzed asymmetric benzylic alkylation of active methylene compounds with racemic diarylmethyl carbonates and pivalates. To the best of our knowledge, this is the first successful example of the dynamic kinetic asymmetric transformation (DYKAT) of secondary benzylic electrophiles via π-benzylpalladium intermediates. The present results provide an enantioconvergent approach to optically active benzylic alkylation products from racemic benzyl alcohol derivatives and prompt further development of related asymmetric catalysis based on the DYKAT process of secondary benzyl electrophiles. Expansion of the scope of nucleophiles and overcoming the naphthalene limitation are currently underway in our laboratory.
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.
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,
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,
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
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
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
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.
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,
Manganese-Catalyzed Late- Stage Aliphatic C H Azidation
Wipf group current literature Manganese-Catalyzed Late- Stage Aliphatic C H Azidation J. Am. Chem. Soc. 2015, 137, 5300 5303 Xiongyi Huang, Tova M. Bergsten, and John T. Groves Department of Chemistry,
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
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
Literature Report. Atroposelective Synthesis of Axially Chiral Arylpyrroles and Styrenes. : Zhong Yan : Ji Zhou :
Literature eport Atroposelective Synthesis of Axially Chiral ylpyrroles and Styrenes eporter Checker Date : Zhong Yan : Ji Zhou : 2017-06-05 Tan, B. et al. J. Am. Chem. Soc. 2017, 139, 1714. Tan, B. et
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
Career Review of Dean Toste I. 2015/9/9 Zhi Ren
Career Review of Dean Toste I 2015/9/9 Zhi Ren Introduction F. Dean Toste, now in UC Berkeley Career: Full Professor since 2009-now Associate Professor 2006-2009 Assistant Professor 2002-2006 Faculty Scientist
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.
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,
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
Palladium-catalyzed sp 3 C H activation. Yan Xu Dong Group Meeting Apr. 2, 2014
Palladium-catalyzed sp 3 C H activation, Yan Xu Dong Group Meeting Apr. 2, 2014 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation:
Denmark Group Meeting. & Electrophilic rearrangement of amides
Denmark Group Meeting Palladium catalyzed Dearomatizationeaction & Electrophilic rearrangement of amides 11 th Bo Peng th Feb. 2014 1 https://maps.google.com 2 Palladium catalyzed Dearomatization eaction
Title. Author(s)Ishiyama, Tatsuo; Oohashi, Zengo; Ahiko, Taka-aki; M. CitationChemistry Letters, 8: Issue Date Doc URL.
Title Nucleophilic Borylation of Benzyl Halides with Bis(p Author(s)Ishiyama, Tatsuo; Oohashi, Zengo; Ahiko, Taka-aki; M CitationChemistry Letters, 8: 7-781 Issue Date 2002-08-05 Doc URL http://hdl.handle.net/2115/56196
Parallel Kinetic Resolution. Group Meeting Timothy Chang
Parallel Kinetic Resolution (PKR) Group Meeting 09 29 2009 Timothy Chang Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584. Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078. KR versus PKR The
Direct Catalytic Cross-Coupling of Organolithium
Literature report Direct Catalytic Cross-Coupling of Organolithium Compounds Reporter: Zhang-Pei Chen Checker: Mu-Wang Chen Date: 02/07/2013 Feringa, B.L.et al. Feringa, B. L. et al. Nature Chem. 2013,
Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C H Borylation
Enabled by Ligand-Controlled C H Borylation Yu Feng, Dane Holte, Jochen Zoller, Shigenobu Umemiya, Leah R. Simke, and Phil S. Baran J. Am. Chem. Soc. 2015, 137, 10160 10163. I. Introduction II. Retrosynthetic
Non-Enzymatic Enantioselective Polyene Cyclizations. Adam Hill Chem 535 May, 2 nd 2013
Non-Enzymatic Enantioselective Polyene Cyclizations Adam Hill Chem 535 May, 2 nd 2013 Enantioselective Polyene Cyclization (?) General Method to Rapidly Build Molecular Complexity (+) Exquisite Stereo-
D. X. Hu Towards Catalytic Enantioselective Halogenation of Alkenes Burns Group
D. X. Hu Towards Catalytic Enantioselective Halogenation of Alkenes Burns Group Literature Review Organic Synthesis 10, 20, 50 Years from Now? Catalytic Enantioselective Halogenation October 6 th, 2012
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,
PhD research with Prof. Lutz H. Gade at the Univ. of Strasbourg. Postdoc in 2003 with Andreas Pfaltz (Basel Switzerland)
idium-catalyzed Asymmetric Isomerization of rimary Allylic Alcohols Mantilli, L., Gerard, D., Torche, S., Besnard, C., Mazet * C. Angew. Chem. Int. Ed., 2009, 48, 1-6 1,n-Glycols as Dialdehyde Equivalents
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...
Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic Asymmetric Synthesis of gamma-thioesters
Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic Asymmetric Synthesis of gamma-thioesters The MIT Faculty has made this article openly available. Please share how this access benefits you.
1. Theoretical Investigation of Mechanisms and Stereoselectivities of Synthetic Organic Reactions
1. Theoretical Investigation of Mechanisms and Stereoselectivities of Synthetic Organic Reactions 2. Copper Catalyzed One-Pot Synthesis of Multisubstituted Quinolinones Hao Wang Denmark Group Presentation
Chromium Arene Complexes
Go through Reviews Chem. Reviews Chem. Soc. Reviews Book by Prof. A. J. Elias Chromium Arene Complexes Complexation of Cr(CO) 3 with ARENES Chromium arene complexes Metal complexation is appealing in organic
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
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.;
The Curtin-Hammett Principle
[B 2 ] G TS2 - G TS1 t [B 1 ] t = ( (G TS2 - G TS1 ) ) e RT ΔG 1 ΔG 21 ΔG 2 So, relative reaction rates depend only on relative transition-state energies, and not on starting-material ground-state energies.
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.
C H Activated Trifluoromethylation
Literature report C H Activated Trifluoromethylation Reporter:Yan Fang Superior:Prof. Yong Huang Jun. 17 th 2013 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation
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,
"-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,
I. Introduction. Peng Zhao. Liu lab
Asymmetric Total Synthesis of Mycoleptodiscin A Shupeng Zhou, Hao Chen, Yijie Luo, Wenhao Zhang and Ang Li Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai
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
Lecture 6: Transition-Metal Catalysed C-C Bond Formation
Lecture 6: Transition-Metal Catalysed C-C Bond Formation (a) Asymmetric allylic substitution 1 u - d u (b) Asymmetric eck reaction 2 3 Ar- d (0) Ar 2 3 (c) Asymmetric olefin metathesis alladium π-allyl
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,*
A Stille or Suzuki reaction is a good choice for this coupling O O because they are functional group tolerant, no radical chemistry F
Chemistry 253 roblem et 3 Due: Friday, ctober 15th ame TF 1. For the following products of cross coupling reactions and indicated bond disconnections, please indicate a reasonable cross coupling protocol
Chiral Anions in Asymmetric Catalysis. Hannah Haley Burke Group Literature Seminar 13 April 2013
Chiral Anions in Asymmetric Catalysis annah aley Burke Group Literature Seminar 13 April 2013 Key Ac2va2on Modes for Asymmetric Catalysis L M X 1 2 Coordinative interaction 'Lewis acid catalysis' Lewis
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
Chapter 5. Nucleophilic aliphatic substitution mechanism. by G.DEEPA
Chapter 5 Nucleophilic aliphatic substitution mechanism by G.DEEPA 1 Introduction The polarity of a carbon halogen bond leads to the carbon having a partial positive charge In alkyl halides this polarity
Literature Report 5. Total Synthesis of Ileabethoxazole, Pseudopteroxazole, and seco-pseudopteroxazole
Literature Report 5 Total Synthesis of Ileabethoxazole, Pseudopteroxazole, and seco-pseudopteroxazole Reporter: Guang-Shou Feng Checker: Lei Shi Date: 2016-04-12 Li, A. et al. Angew. Chem. Int. Ed. 2016,
Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group.
Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group. akatani, Y.; Koizumi, Y.; Yamasaki, R.; Saito, S. rg. Lett. 2008, 10, 2067-2070. An Annulation Reaction for the Synthesis
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
The Synthesis of Molecules Containing Quaternary Stereogenic Centers via the Intramolecular Asymmetric Heck Reaction
The Synthesis of Molecules Containing Quaternary Stereogenic Centers via the Intramolecular Asymmetric Heck Reaction Reported by Eric P. Gillis April 19, 2007 INTRODUCTION The enantioselective synthesis
Learn- More. Weblinks. PAPER 5: Organic Chemistry- II MODULE 23 : SE2 Reactions
Learn- More Weblinks q http://www.scribd.com/doc/25905271/aliphatic-electrophilic-substitution-reactions q http://en.wikipedia.org/wiki/electrophilic_substitution q http://www.scribd.com/doc/76229481/electrophilic-substitution
Efficient enantioselective hydrogenation of quinolines catalyzed by conjugated microporous polymers with embedded chiral BINAP ligand
Chinese Journal of Catalysis 36 (2015) 1170 1174 available at www.sciencedirect.com journal homepage: www.elsevier.com/locate/chnjc Communication Efficient enantioselective hydrogenation of quinolines
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
N,B-Bidentate Boryl Ligand-Supported Iridium Catalyst for C H Borylation
N,B-Bidentate Boryl Ligand-Supported Iridium Catalyst for C H Borylation Reporter: Bo Song Checker: Yue Ji Date: 2017/01/03 Wang, G.; Liu, L.; Wang, H.; Li, P. J. Am. Chem. Soc. 2017, 139, ASAP. Pengfei
Chiral Supramolecular Catalyst for Asymmetric Reaction
Chiral Supramolecular Catalyst for Asymmetric Reaction 2017/1/21 (Sat.) Literature Seminar Taiki Fujita (B4) 1 Introduction Rational design of chiral ligands remains very difficult. Conventional chiral
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
Asymmetric Palladium Catalyzed Cross-Coupling Reactions. Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1
Asymmetric Palladium Catalyzed Cross-Coupling Reactions Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1 Palladium Catalyzed Cross-Coupling Reactions 2 Kumada/Negishi Cross-Coupling Kumada:
Carbon-Carbon Bond Formation Driven by the Water-Gas Shift Reaction
Carbon-Carbon Bond Formation Driven by the Water-Gas Shift Reaction Zachery Matesich 28 March 2017 2 Projects Allyl electrophile scope Asymmetric allylation Alternative approaches 3 Water-Gas Shift Reaction
CHAPTER FOUR. The Development of an Asymmetric Tsuji Allylation Reaction
402 CHAPTER FUR The Development of an Asymmetric Tsuji Allylation Reaction 4.1 Introduction The catalytic asymmetric synthesis of all-carbon quaternary stereocenters stands as a significant challenge in
CATALYSIS MULTICATALYST SYSTEM IN ASYMMETRIC. Wiley. Department of Chemistry
MULTICATALYST SYSTEM IN ASYMMETRIC CATALYSIS JIAN ZHOU Shanghai Key Laboratory of Green Chemistry and Chemical Processes Department of Chemistry East China Normal University Shanghai, China Wiley Preface
Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid
Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid Shiqing Xu, Akimichi Oda, Thomas Bobinski, Haijun Li, Yohei Matsueda, and Ei-ichi Negishi Angew. Chem. Int. Ed. 2015,
Construction of C-C or C-N Bond via C-H Activation ~Chemistry of Yong-Qiang Tu~
Literature Seminar 2010.5.26 Yao u(2) Construction of C-C or C-N Bond via C-H Activation ~Chemistry of Yong-Qiang Tu~ Contents: 1. Yong-Qiang Tu's Profile 2.LatestWorkofProfessorTu 2-1. C-H Activation
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.
Nucleophilic Substitution and Elimination
Nucleophilic Substitution and Elimination Alkyl halides react with a nucleophile in one of two ways. Either they eliminate an X to form an alkene, or they undergo a substitution with the nucleophile, Nu,
11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations Based on McMurry s Organic Chemistry, 6 th edition 2003 Ronald Kluger Department of Chemistry University of Toronto Alkyl Halides
Preparation of Alkyl Halides, R-X. Reaction of alkanes with Cl 2 & Br 2 (F 2 is too reactive, I 2 is unreactive): R + X X 2.
Preparation of Alkyl alides, R-X Reaction of alkanes with Cl 2 & Br 2 (F 2 is too reactive, I 2 is unreactive): UV R + X 2 R X or heat + X This mechanism involves a free radical chain reaction. A chain
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
CH 3 TMG, DMF N H 3 CO 2 S. (PPh 3 ) 2 Pd 0
1. (a) rovide a reasonable mechanism for the following transformation. I S 2 C 3 C 3 ( 3 ) 2 2, CuI C 3 TMG, DMF 3 C 2 S TMG = Me 2 Me 2 ICu ( 3 ) 2 0 I S 2 C 3 S 2 C 3 Cu I 3 3 3 C 2 S I 3 3 3 C 2 S 3
Rhodium Catalyzed Alkyl C-H Insertion Reactions
Rhodium Catalyzed Alkyl C-H Insertion Reactions Rh Rh Jeff Kallemeyn 5/17/05 1. Cyclopropanation The Versatile and Reactive Rhodium Carbene R + Et Rh 2 (Ac) 4 R C 2 Et N 2 2. [2,3] sigmatropic rearrangement
Nucleophilic Fluorination. Souvik Rakshit Burke group Literature Seminar July 13, 2013
Nucleophilic Fluorination Souvik Rakshit Burke group Literature Seminar July 13, 2013 Relevance 20% of pharmaceuticals contain fluorine 5-fluorouracil Antineoplastic agent, 1957 Lipitor (Atorvastatin)
Stereoselective reactions of enolates
1 Stereoselective reactions of enolates Chiral auxiliaries are frequently used to allow diastereoselective enolate reactions Possibly the most extensively studied are the Evan s oxazolidinones These are
1/4/2011. Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds
Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds The Acidity of the Hydrogens of Carbonyl Compounds: Enolate Anions Hydrogens on carbons to carbonyls are unusually acidic
Chiral Amplification. Literature Talk Fabian Schneider Konstanz, Universität Konstanz
Chiral Amplification Literature Talk Fabian Schneider Konstanz, 18.10.2017 Overview 1) Motivation 2) The nonlinear Effect in asymmetric catalysis - First encounters - Basic principles - Formalization and
Organic Reactions Susbstitution S N. Dr. Sapna Gupta
Organic Reactions Susbstitution S N 2 Dr. Sapna Gupta Kinetics of Nucleophilic Reaction Rate law is order of reaction 0 order is when rate of reaction is unaffected by change in concentration of the reactants
Enantioselective Protonations
Enantioselective Protonations Marc Timo Gieseler 25.02.2013 15.03.2013 Group Seminar AK Kalesse 1 verview Introduction Enantioselective Protonation of Cyclic Substrates Enantioselective Protonation of
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
Branched-Regioselective Hydroformylation with Catalytic Amounts of a Reversibly Bound Directing Group
1/12 Branched-egioselective ydroformylation with Catalytic Amounts of a eversibly Bound Directing Group h(i)/me C/ 2 MS 4A branched major by Christian U. Grünanger and Bernhard Breit Angew. Chem. Int.
Title. Author(s)Ishiyama, Tatsuo; Itoh, Yoshiya; Kitano, Takahiro; M. CitationTetrahedron Letters, 38(19): Issue Date
Title Synthesis of arylboronates via the palladium(0)-cata triflates Author(s)Ishiyama, Tatsuo; Itoh, Yoshiya; Kitano, Takahiro; M CitationTetrahedron Letters, 38(19): 3447-3450 Issue Date 1997-05-12 Doc
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
Recent Advances in IMCRs (Passerini and Ugi Reac5ons) Anil Kumar Gupta Group Mee5ng May 16,2008
Recent Advances in IMCRs (Passerini and Ugi Reac5ons) Anil Kumar Gupta Group Mee5ng May 16,2008 Mul5component Reac5ons 100 % yield Simple Total Conversion One pot safe Resource effec5ve Environmental Friendly
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
Fe-Catalyzed reactions of 2-chloro-1,7-dienes and allylmalonates
Fe-Catalyzed reactions of 2-chloro-1,7-dienes and allylmalonates David Nečas a, Pavel Drabina b, Miloš Sedlák b and Martin Kotora a,c a Department of Organic and Nuclear Chemistry, and Center for Structural
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
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.
Self-stable Electrophilic Reagents for Trifluoromethylthiolation. Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date:
Self-stable Electrophilic Reagents for Trifluoromethylthiolation Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date: 2017-12-25 Content Introduction Trifluoromethanesulfenates: Preparation and reactivity
Hybridization of Nickel Catalysis and Photoredox Catalysis. Literature seminar#1 B4 Hiromu Fuse 2017/02/04(Sat)
Hybridization of Nickel Catalysis and Photoredox Catalysis Literature seminar#1 B4 Hiromu Fuse 2017/02/04(Sat) Introduction Novel cross coupling was reported! Highly selective sp 3 C-H functionalization!
Enantioselective Borylations. David Kornfilt Denmark Group Meeting Sept. 14 th 2010
Enantioselective Borylations David Kornfilt Denmark Group Meeting Sept. 14 th 2010 30.000-foot View Enantioenriched Organoboranes What to do with them Crudden C. M. et. al., Eur. J. Org. Chem. 2003, 46
Recent applications of chiral binaphtholderived phosphoric acid in catalytic asymmetric reactions
Recent applications of chiral binaphtholderived phosphoric acid in catalytic asymmetric reactions 1. Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, ASAP. 2. Storer, R. L.; Carrera, D. E.;
Columbia University C99ORG12.DOC S3443D Summer 99 Professor Grace B. Borowitz Exam No. 2 June 14, 1999
olumbia University 99RG12.D SD Summer 99 Professor Grace B. Borowitz Exam No. 2 June 1, 1999 Name: Sterie hemistry Grade: Please use a non-red pen. Answer questions in the provided space. If you write
Mild Cobalt-Catalyzed Hydrocyanation of Olefins with Tosyl Cyanide
Mild Cobalt-Catalyzed ydrocyanation of lefins with Tosyl Cyanide 1 3 2 + Ts Co cat., Si 3 Et, 1-3 h, T 1 2 3 Gaspar, B.; Carreira, E. M. Angew. Chem. Int. Ed. ASAP Current Literature Kalyani Patil 12 May
C H activation of aliphatic amines without unnecessary mask M2 Takaya Togo
C H activation of aliphatic amines without unnecessary mask 2017.11.25 M2 Takaya Togo 1 Outline 1.Introduction 2.Free amines as DG Discovery of new activation mode Mechanistic studies Application of the
CHEM 251 (4 credits): Description
CHEM 251 (4 credits): Intermediate Reactions of Nucleophiles and Electrophiles (Reactivity 2) Description: An understanding of chemical reactivity, initiated in Reactivity 1, is further developed based
Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides
Negishi Coupling of Secondary Alkylzinc alides with Aryl Bromides and Chlorides X X = Br, Cl 2 1 ZnBr 1, 2 = Alkyl Cat. Pd(OAc) 2 Ligand TF/Toluene rt or 60 o C 1 2 J. Am. Chem. Soc. 2009, ASAP Article
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols B() 2 H H B() 2 H H Hu, X.-D.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.
Hydrogen-Mediated C-C Bond Formation
EPFL - ISIC - LSPN Hydrogen-Mediated C-C Bond Formation History and selected examples The Research of Prof. Michael Krische (University of Texas at Austin) LSPN Group Seminar Mathias Mamboury Table of
Module No and Title. PAPER No: 5 ; TITLE : Organic Chemistry-II MODULE No: 25 ; TITLE: S E 1 reactions
Subject Chemistry Paper No and Title Module No and Title Module Tag 5; Organic Chemistry-II 25; S E 1 reactions CHE_P5_M25 TABLE OF CONTENTS 1. Learning Outcomes 2. Introduction 3. S E 1 reactions 3.1
Morita Baylis Hillman Reaction. Aaron C. Smith 11/10/04
Morita Baylis Hillman Reaction Aaron C. Smith 11/10/04 Outline 1. Background 2. Development of Asymmetric Variants 3. Aza-Baylis Hillman Reaction 4. Applications of Baylis Hillman Adducts Outline 1. Background
Non-Linear Effects in Asymmetric Catalysis: A Useful Tool in Understanding Reaction Mechanisms. Group Meeting Aaron Bailey 12 May 2009
Non-Linear Effects in Asymmetric Catalysis: A Useful Tool in Understanding Reaction chanisms Group eting Aaron Bailey 12 May 2009 What is a Non-Linear Effect? In asymmetric catalysis, the ee (er) of the
Supporting Information
Supporting Information Incorporation of a Sugar Unit into a C C N Pincer Pd Complex Using Click Chemistry and Its Dynamic Behavior in Solution and Catalytic Ability toward the Suzuki Miyaura Coupling in
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.