Literature DB >> 29711141

Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation.

Christian Girard1, Henri B Kagan2.   

Abstract

Who would have thought before 1986 that an enantiomerically impure catalyst could give a product in an asymmetric synthesis with an enantiomeric excess higher than that of the catalyst? Until then it was assumed that the ee value of the product (eeprod ) from an asymmetric synthesis was linearly correlated to the ee value of the chiral auxiliary (eeaux )-in fact a large deviation is possible (see diagram). These nonlinear effects are not only of academic interest since they have a variety of practical uses, which are highlighted in this review. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Keywords:  Asymmetric amplification; Asymmetric catalysis; Asymmetric synthesis; Autocatalysis; Chiral auxiliaries

Year:  1998        PMID： 29711141     DOI： 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO;2-1

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  21 in total

1.  The origin of biological homochirality.

Authors:  Donna G Blackmond
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  2011-10-27       Impact factor: 6.237

Review 2.  The origin of biological homochirality.

Authors:  Donna G Blackmond
Journal:  Cold Spring Harb Perspect Biol       Date:  2010-03-31       Impact factor: 10.005

3.  Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: insights from computation and experiment.

Authors:  Jeffrey C Holder; Lufeng Zou; Alexander N Marziale; Peng Liu; Yu Lan; Michele Gatti; Kotaro Kikushima; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-09-27       Impact factor: 15.419

4.  Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.

Authors:  En-Chih Liu; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2019-03-21       Impact factor: 15.419

5.  Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.

Authors:  Michael W Gribble; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2020-06-11       Impact factor: 15.419

6.  Mechanistic basis for high stereoselectivity and broad substrate scope in the (salen)Co(III)-catalyzed hydrolytic kinetic resolution.

Authors:  David D Ford; Lars P C Nielsen; Stephan J Zuend; Charles B Musgrave; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-10-07       Impact factor: 15.419

7.  Enantioselective Copper(I)-Catalyzed Alkynylation of Oxocarbenium Ions to Set Diaryl Tetrasubstituted Stereocenters.

Authors:  Srimoyee Dasgupta; Thomas Rivas; Mary P Watson
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-25       Impact factor: 15.336

Review 8.  Synthesis and Application of the Transition Metal Complexes of α-Pyridinyl Alcohols, α-Bipyridinyl Alcohols, α,α'-Pyridinyl Diols and α,α'-Bipyridinyl Diols in Homogeneous Catalysis.

Authors:  Tegene Tole; Johannes Jordaan; Hermanus Vosloo
Journal:  Molecules       Date:  2018-04-12       Impact factor: 4.411

9.  Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.

Authors:  En-Chih Liu; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2021-04-02       Impact factor: 15.419

Review 10.  Recommended Tests for the Self-Disproportionation of Enantiomers (SDE) to Ensure Accurate Reporting of the Stereochemical Outcome of Enantioselective Reactions.

Authors:  Jianlin Han; Alicja Wzorek; Karel D Klika; Vadim A Soloshonok
Journal:  Molecules       Date:  2021-05-07       Impact factor: 4.411
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