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Lithium Ephedrinate Mediated Aldol Reaction of Arylacetonitriles: Thermodynamic Control of Enantioselectivity
Author(s) -
Carlier Paul R.,
Lam Weldon W.F.,
Wan Nan Chi,
Williams Ian D.
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(19980904)37:16<2252::aid-anie2252>3.0.co;2-z
Subject(s) - aldol reaction , stereocenter , lithium (medication) , chemistry , organic chemistry , enantioselective synthesis , catalysis , biology , endocrinology
Deracemization , the conversion of a racemic mixture into an enantiomerically enriched material, is achieved with the retro‐aldol reaction of rac ‐ 1 in the presence of lithium (−)‐ephedrinate [Eq. (1)]. Remarkably, two stereogenic centers are simultaneously deracemized. This reaction shows that efficient thermodynamic control of the enantioselectivity of aldol reactions is possible