Nonlinear Effects In Asymmetric Catalysis

被引:409
|
作者
Satyanarayana, Tummanapalli [1 ]
Abraham, Susan [1 ]
Kagan, Henri B. [1 ]
机构
[1] Univ Paris 11, CNRS, Inst Chim Mol & Mat Orsay, Lab Catalyse Mol,UMR 8182, F-91405 Orsay, France
关键词
asymmetric catalysis; autocatalysis; chiral auxiliaries; nonlinear effects; scalemic catalysts; HETERO-DIELS-ALDER; ENANTIOSELECTIVE CONJUGATE ADDITION; CHIRAL-SYMMETRY-BREAKING; ALPHA-AMINO-ACIDS; MANNICH-TYPE REACTIONS; CARBONYL-ENE REACTION; C BOND FORMATION; LEWIS-ACID; ENANTIOMERIC EXCESS; ALDOL CONDENSATION;
D O I
10.1002/anie.200705241
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Graph Presented) There is a need for the preparation of enantiomerically pure compounds for various applications. An efficient approach to achieve this goal is asymmetric catalysis. The chiral catalyst is usually prepared from a chiral auxiliary, which itself is derived from a natural product or by resolution of a racemic precursor. The use of non-enantiopure chiral auxiliaries in asymmetric catalysis seems unattractive to preparative chemists, since the anticipated enantiomeric excess (ee) of the reaction product should be proportional to the ee value of the chiral auxiliary (linearity). In fact, some deviation from linearity may arise. Such nonlinear effects can be rich in mechanistic information and can be synthetically useful (asymmetric amplification). This Review documents the advances made during the last decade in the use of nonlinear effects in the area of organometallic and organic catalysis. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:456 / 494
页数:39
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