"-Amino Acids: Function and Synthesis
|
|
|
- Anthony Booker
- 6 years ago
- Views:
Transcription
1 "-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, S..; DeGrado, W. F. Chem. ev. 2001, 101, Enantioselective Synthesis of "-Amino Acids; Juaristi, E., Ed.; Wiley-VC: ew York, Seebach, D.; Matthews, J. L. Chem. Commun. 1997, Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.!-Amino Acids vs. "-Amino Acids!-Amino acids "-Amino acids substitution positions 2 configurations: (), (S) substitution positions configurations: (2), (2S), (3), (3S), (,), (,S), (S,), (S,S) 2 "-Amino acids allow for greater diversity. Extra C-C bond potenially allows for increased diversity in secondary structures. Seebach, D.; Matthews, J. L. Chem. Commun. 1997,
2 2
3 ! 3 Substituted!-Amino Acids Arndt-Eistert eaction 1) ClC 2, 3, TF 2) C 2 2, 2, 80% 2 Ag 2C, 3, 95% Wolff earrangement Enantiomercally pure!-amino acids are prepared from the appropriate "-amino acid. earrangement occurs with retention of stereochemistry. Epimerization is rarely observed. Enantioselective Synthesis of!-amino Acids; Juaristi, E., Ed.; Wiley-VC: ew York, 1997.! 2,3 Substituted!-Amino Acids 2 eq. LDA / LiCl Li Li I 95% yield Li Li Electrophile approaches from above! 3 -Amino acids derived from the Arndt-Eistert method can be further elaborated to! 2,3 -amino acids. igh diastereoselectivities are observed in alkylations. Enantioselective Synthesis of!-amino Acids; Juaristi, E., Ed.; Wiley-VC: ew York, 1997.! 2 Substituted!-Amino Acids TiCl 4, 3 BzC 2Cl Bz ydrolysis 2 Ti Electrophile approaches from below Evans' chiral auxiliary alkylation produces! 2 -amino acids of high enantiomeric purity. Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, Catalytic Asymmetric Addition of -Benzylhydroxylamine 30 mol% MgBr 2, Ligand 2 (1.1 eq), C 2Cl 2 =,,, and i-pr 74-80% yield 87-95% ee This is the first highly enantioselective catalytic conjugate amine addition. The other enatiomeric series can be accessed through use of Y(Tf) 3 or Yb(Tf) 3 though ee's are below 60%. Substitution on olefin limited to alkyl groups. igh catalyst loading. Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120,
4 Kinetic esolution of!-amino Amide 100 mol% MgBr 2, Ligand 2 (0.5 eq), C 2Cl 2 racemic 47% yield 34% yield 47% ee () 60% ee (S) ee of entioselective reaction increases over time but yield decreases. Minor enantiomer undergoes aminolysis faster than major enantiomer. Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, Amine Conjugate Additions to Cinnamates 30 mol% MgX 2, Ligand Ar (2.2 eq), C 2Cl 2 Ar 53-87% yield 60-96% ee X= I, (Cl 4) First highly enantioselective conjugate amine addition to cinnamates. -Benzylhydroxylamine is more reactive than -benzylhydroxylamine and the pyrrolidinone cinnamate also more reactive than the corresponding pyrazole substrate. Sibi, M. P.; Liu, M. rg. Lett. 2000, 2,
5 rganocatalytic Addittion of Azide TMS 3, C 2, catalyst 3 Toluene, 25 C i-pr % yield % ee Boc tbu cy Boc Catalyst is an organic molecule which gives it obvious benefits.!-turn is necessary for selectivity. Guerin, D. J.; orstmann, T. E.; Miller, S. Angew. Chem. Int. Ed. 2000, 39, rganocatalytic Approach To Cyclic!-Amino Acids Cl ac 3, 2/ 2 68% yield 89% ee 1) acl 2, i-butene, a 2P 4 2; 98% 2) Br, DBU 3) s 4, M; 86%.C. gives quick access to highly functionalized!-amino acids. Wipf, P.; Wang, X. Tetrahedron. Let. 2000, 41, rgano Catalytic Approachs To "-Amino Carbonyls, -30 C Cl 4 91% yield 98% ee > 100:1 dr Z / 2, -20 C Cl 4 Z 1 C 70-98% yield 90-99% ee a, eflux, 2.5 hrs. 80% yield TBS Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, Summary Lengthening!-amino acids by one carbon does not lead to chaos, but new secondary folding structures. "-Peptides form secondary structures with greater stability than!-peptides. The metabolic stability of "-peptides can be utilized in drug design. Asymmetric catalysis should provide inexpensive and quick access to novel "-amino acids. 5
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,
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 +
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,
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)
Asymmetric Alklylation of Enolates
Asymmetric Alklylation of Enolates M with material from A G Meyers http://faculty.chemistry.harvard.edu/myers/pages/chem-215-handouts 745 rganic Synthesis Spring 2015 Asymmetric Alkylation - eed to control
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
Catalytic Asymmetric Acyl Halide-Aldehyde Cyclocondensation Reactions of Substituted Ketenes
Catalytic Asymmetric Acyl Halide-Aldehyde Cyclocondensation eactions of Substituted Ketenes Scott G. elson, Cheng Zhu, and Xiaoqiang Shen J. Am. Chem Soc. 2004, 126, 14-15. Michael C. Myers, Literature
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.
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
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
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
Epoxidation with Peroxy Acids
Epoxidation with Peroxy Acids RC 3 R C more reactive more likely Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M.; Rastelli, A. J. rg. Chem. 2000, 65, 2030. Singleton, D. A.; Merrigan, S. R.; Liu, J.; ouk,
Stereoselective reactions of enolates: auxiliaries
1 Stereoselective reactions of enolates: auxiliaries Chiral auxiliaries are frequently used to allow diastereoselective enolate reactions Possibly the most extensively studied are the Evan s oxazolidinones
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
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
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
Conjugate (1,4-) addition
1 Conjugate (1,4-) addition uc R 1 R 2 uc R 1 R 2 uc R 1 E R 2 E ucleophilic attack on C=C bond normally requires electron deficient alkene Know as 1,4-addition or conjugate addition As enolate formed
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
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
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
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
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,
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.
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...
Bifunctional Asymmetric Catalysts: Design and Applications. Junqi Li CHEM Sep 2010
Bifunctional Asymmetric Catalysts: Design and Applications Junqi Li CHEM 535 27 Sep 2010 Enzyme Catalysis vs Small-Molecule Catalysis Bronsted acid Lewis acid Lewis acid Bronsted base Activation of both
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.
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
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,
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
Requirements for an Effective Chiral Auxiliary Enolate Alkylation
Requirements for an Effective Chiral Auxiliary Enolate Alkylation 1. Xc must be low cost, and available in both enentiomeric forms 2. The cleavage of Xc from the substrate must occur under mild enough
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
Spiro Monophosphite and Monophosphoramidite Ligand Kit
Spiro Monophosphite and Monophosphoramidite Ligand Kit metals inorganics organometallics catalysts ligands custom synthesis cgm facilities nanomaterials 15-5162 15-5150 15-5156 15-5163 15-5151 15-5157
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
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.
Organocatalytic Umpolung via N- Heterocyclic Carbenes. Qinghe Liu Hu Group Meeting August 20 th 2015
rganocatalytic Umpolung via N- Heterocyclic Carbenes Qinghe Liu Hu Group Meeting August 20 th 2015 Contents Part 1: Introduction Part 2: N-Heterocyclic carbene-catalyzed umpolung: classical umpolung, conjugated
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.
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
Stereoselective Organic Synthesis
Stereoselective rganic Synthesis Prabhat Arya Professor and Leader, Chemical Biology Program Dean, Academic Affairs, Institute of Life Sciences (An Associate Institute of University of yderabad Supported
Total synthesis of Spongistatin
Literature Semminar 1. Introduction: Total synthesis of Spongistatin Chen Zhihua (M2) Isolation: Pettit et al. J. rg. Chem. 1993, 58, 1302. Kitagawa et al. Tetrahedron Lett. 1993, 34, 1993. Fusetani et
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
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.;
Asymmetric Catalysis by Chiral Hydrogen-Bond Donors
Asymmetric Catalysis by Chiral Hydrogen-Bond Donors Angew. Chem. Int. Ed., 2006, 45, 1520~1543 Mark S. Taylor and Eric N. Jacobsen* Current Literature Presentation Zhenglai Fang Wipf s Group at Pitt Zhenglai
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
Stereoselective Organic Synthesis
Stereoselective rganic Synthesis Prabhat Arya Professor and Leader, Chemical Biology Program Dean, Academic Affairs, Institute of Life Sciences (An Associate Institute of University of yderabad Supported
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.
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
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,
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
Advanced Organic Chemistry
D. A. Evans, G. Lalic Question of the day: Chemistry 530A TBS Me 2 C Me toluene, 130 C 70% TBS C 2 Me H H Advanced rganic Chemistry Me Lecture 16 Cycloaddition Reactions Diels _ Alder Reaction Photochemical
Total Synthesis of Oxazolomycin A
Total Synthesis of xazolomycin A Me xazolomycin A Me Eto, K.; Yoshino, M.; Takahashi K.; Ishihara, J.; atakeyama S. rg. Lett. 2011, 13, 5398 Dimas Paz Wipf group- Current Literature ctober 8, 2011 Dimas
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
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
Suggested solutions for Chapter 32
s for Chapter 32 32 PBLEM 1 Explain how the stereo- and regio- chemistry of these reactions are controlled. Why is the epoxidation only moderately diastereoselective, and why does the amine attack where
CEM 852 Final Exam. May 5, 2011
CEM 852 Final Exam May 5, 2011 This exam consists of 8 pages. Please make certain that your exam has all of the necessary pages. Total points possible for this exam are 150. In answering your questions,
Solvias (R)-MeO-BIPHEP Ligand Kit
metals inorganics organometallics catalysts ligands custom synthesis cgm facilities nanomaterials Catalog # 96-3655 Solvias ()- and (S)-Me BIE Ligand Kits for asymmetric hydrogenation and other catalytic
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
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
[3,3]-Sigmatropic rearrangements
![[3,3]-Sigmatropic rearrangements](/thumbs/75/71504906.jpg "[3,3]-Sigmatropic rearrangements")
1 [3,3]-Sigmatropic rearrangements heat R 1 R 3 R 1 R 3 R 1 R 3 A class of pericyclic reactions whose stereochemical outcome is governed by the geometric requirements of the cyclic transition state Reactions
CHT402 Recent Advances in Homogeneous Catalysis Organocatalysis Workshop
CT402 Recent Advances in omogeneous Catalysis rganocatalysis Workshop Dr Louis C. Morrill School of Chemistry, Cardiff University Main Building, Rm 1.47B MorrillLC@cardiff.ac.uk For further information
Direct, Catalytic Hydroaminoalkylation of Unactivated Olefins with N-Alkyl Arylamines
Current Literature - May 12, 2007 Direct, Catalytic ydroaminoalkylation of Unactivated lefins with -Alkyl ylamines ' '' Ta[ 2 ] 5 (4-8 mol%), 160-165 o C 24-67h 66-95% ' '' S. B. erzon and J. F. artwig,
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,
Synthesis and Utility of α Silylamines: A Brief Overview. Literature Presentation 4/6/2K4 Dave Ballweg
Synthesis and Utility of α Silylamines: A Brief verview Literature Presentation 4/6/2K4 Dave Ballweg Utility of Amines 1. Amines are ubiquitous in organic/medicinal chemistry 2. Important precursers to
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
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
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
ISCHIA ADVANCED SCHOOL OF ORGANIC CHEMISTRY
ewis acid activation ewis base activation ISCIA ADVACED SC F GAIC CEMISTY Dual in Enantioselective Synthesis of Cyanohydrins Me A A Me UM ewis base catalysis is the process by which an electronpair donor
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.
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.
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
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
Disulfonimide-Catalyzed Asymmetric Vinylogous and Bisvinylogous Mukaiyama Aldol Reactions
Disulfonimide-Catalyzed Asymmetric Vinylogous and Bisvinylogous Mukaiyama Aldol eactions atjen, L. Garcia-Garcia, P., Lay, F., Beck, M. E., List, B.; Angew. Chem. Int. Ed. 2010, ASAP. Convergent Total
Organocatalytic stereoselective [8+2] and [6+4] cycloadditions
![Organocatalytic stereoselective [8+2] and [6+4] cycloadditions](/thumbs/85/92727022.jpg "Organocatalytic stereoselective [8+2] and [6+4] cycloadditions")
rganocatalytic stereoselective [8+2] and [6+4] cycloadditions Joel Walker Current Literature March 4 th, 2017 Mose, R.; Preegel, G.; Larsen, J.; Jakobsen, S.; Iversen, E..; Jørgensen, K. A. Nature Chem.
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
Recent Development in. Tandem Radical Reactions (TRR)
ecent Development in Tandem adical eactions (T) Feng u Jan. 13, 2006 Contents Brief Introduction of the istory of T Definition of T Intramolecular T Intermolecular T T as Key Steps in Total Synthesis of
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.;
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
Name: CHEM 633: Advanced Organic Chemistry: Physical Final Exam. Please answer the following questions clearly and concisely.
Name: 1 CEM 633: Advanced rganic Chemistry: Physical Final Exam Please answer the following questions clearly and concisely. You may write your answers in the space provided and/or on additional pages.
Catalytic Asymmetric Pauson-Khand Reaction. Won-jin Chung 02/25/2003
Catalytic Asymmetric Pauson-Khand eaction U. Khand; G.. Knox; P. L. Pauson; W. E. Watts J. Chem. Soc. Chem. Commun. 1971, 36 Won-jin Chung 02/25/2003 The General Pattern of the Pauson-Khand eaction Co
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
Chiral Brønsted Acid Catalysis
another. 1 One interesting aspect of chiral Brønsted acid catalysis is that the single s orbital of hydrogen Chiral Brønsted Acid Catalysis Reported by Matthew T. Burk December 3, 2007 INTRODUCTION The
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 )
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,
CHEM 330. Final Exam December 5, 2014 ANSWERS. This a closed-notes, closed-book exam. The use of molecular models is allowed
CEM 330 Final Exam December 5, 2014 Your name: ASWERS This a closed-notes, closed-book exam The use of molecular models is allowed This exam consists of 12 pages Time: 2h 30 min 1. / 30 2. / 30 3. / 30
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,
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.
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
VI. Metal alkyls from oxidative addition / insertion
V. Metal alkyls from oxidative addition / insertion A. Carbonylation - C insertion very facile, metal acyls easily cleaved, all substrates which undergo oxidative addition can in principle be carbonylated.
Organocopper Chemistry
rganocopper Chemistry ave a great historical importance, but still remain highly useful reactions. If not the first organometallic reactions developed they are among the first. Most often used in conjugate
Organic Cumulative Exam January 26, 2017
rganic Cumulative Exam January 26, 2017 Answer only three the six questions. o more than three question answers will be graded any work not to be considered must be clearly marked as such. Clearly indicate
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
Functionalization of C O Bonds. Stefan McCarver. MacMillan Lab Group Meeting
Functionalization of C Bonds Stefan McCarver MacMillan Lab Group eting November 23 rd, 2016 Functionalization of C Bonds "X" X homolytic cleavage catalyst M oxidative addition Why is C Bond Manipulation
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
Lecture 1 ADVANCED SYNTHESIS Stereochemistry Introduction
ecture 1 ADVACED YTEI tereochemistry Introduction ne of the most important issues in modern organic synthesis ost natural compounds are enantiomerically pure Frequently different enantiomers have different
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
Organocopper Reagents
rganocopper eagents General Information!!! why organocopper reagents? - Efficient method of C-C bond formation - Cu less electropositive than Li or Mg, so -Cu bond less polarized - consequences: 1. how
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
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,
A 1,3 Strain and the Anomeric Effect. Michael Shaghafi Chem. Topics Feb. 6, 2012
A 1,3 Strain and the Anomeric Effect Michael Shaghafi Chem. Topics Feb. 6, 2012 Introduction: Definition of A 1,3 Strain m L L m m 3 L 3 1 1 otation about σ-bond between α-stereocenter and olefin is associated
CHO. OMe. endo. xylene, 140 o C, 2 h 70% 1. CH 2 (OMe) 2, MeOH TsOH, rt 2. Bu 2 O, 1,2-dichloroethane 140 o C, 2 h 3. 6 M HCl, THF, rt 44%
VII Abstracts 2010 p1 2.4.12 Arene rganometallic Complexes of Chromium, Molybdenum, and Tungsten M. Uemura This review is an update to Section 2.4 and covers the literature from 1999 to 2010. (h 6 -Arene)chromium
JACS ASAP Article: Published 3/12/08. Lei Jiao, Changxia Yuan and Zhi-Xiang Yu. Current Literature: 3/29/08. David Arnold
Tandem h(i)-catalyzed [(5+2)+1] Cycloaddition/Aldol eaction for the Construction of Linear Triquinane Skeleton: Total Syntheses of (+)-irsutene and (+)-1- Desoxyhypnophilin JACS ASAP Article: Published