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Review
. 1998 Nov 16;37(21):2922-2959.
doi: 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO;2-1.

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

Christian Girard  1 , Henri B Kagan  2
Affiliations
Review

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

Christian Girard et al. Angew Chem Int Ed Engl. .

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.

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

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