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Enantioselective Generation of Benzylic Stereocenters Mediated by a Remote Sulfoxide
Author(s) -
García Ruano José L.,
Carreño M. Carmen,
Toledo Miguel A.,
Aguirre José M.,
Aranda M. Teresa,
Fischer Jean
Publication year - 2000
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 - 10.1002/1521-3773(20000804)39:15<2736::aid-anie2736>3.0.co;2-m
Subject(s) - stereocenter , enantioselective synthesis , sulfoxide , lithium diisopropylamide , stereoselectivity , chemistry , reagent , tetrahydrofuran , mediation , stereochemistry , medicinal chemistry , organic chemistry , catalysis , deprotonation , political science , ion , solvent , law
ortho ‐Sulfinyl‐substituted benzyllithium reagents react with aldehydes and ketones to afford, after desulfurization with Raney‐Nickel, stereoselective access to benzylic stereocenters [Eq. (1)]. This is the first efficient asymmetric 1,4‐induction with mediation by a sulfoxide group. LDA=lithium diisopropylamide; Tol=tolyl; TIPS=triisopropylsilyl.