Premium
Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation
Author(s) -
Girard Christian,
Kagan Henri B.
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981116)37:21<2922::aid-anie2922>3.0.co;2-1
Subject(s) - enantioselective synthesis , stereoselectivity , catalysis , enantiomer , product (mathematics) , nonlinear system , diagram , enantiomeric excess , value (mathematics) , variety (cybernetics) , mathematics , chemistry , organic chemistry , physics , statistics , geometry , quantum mechanics
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 ( ee prod ) from an asymmetric synthesis was linearly correlated to the ee value of the chiral auxiliary ( ee aux )—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.