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Organocatalytic Enantioselective Nucleophilic Vinylic Substitution
Author(s) -
Poulsen Thomas B.,
Bernardi Luca,
Bell Mark,
Jørgensen Karl Anker
Publication year - 2006
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/anie.200602275
Subject(s) - enantioselective synthesis , stereocenter , alkene , chemistry , substitution (logic) , nucleophilic substitution , optically active , nucleophile , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , computer science , programming language
The clash of hybridizations : A tailored phase‐transfer organocatalyst merges sp 3 ‐ and sp 2 ‐hybridized carbon atoms by catalyzing the first enantioselective vinylic substitution (see scheme; EWG=electron‐withdrawing group). The method provides access to optically active compounds possessing vinyl‐substituted quaternary stereocenters with control of the alkene configuration.