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Catalytic Enantioselective Synthesis of β‐Lactams: Intramolecular Kinugasa Reactions and Interception of an Intermediate in the Reaction Cascade
Author(s) -
Shintani Ryo,
Fu Gregory C.
Publication year - 2003
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.200352103
Subject(s) - stereocenter , enantioselective synthesis , intramolecular force , chemistry , electrophile , oxazoline , catalysis , stereochemistry , combinatorial chemistry , cascade , medicinal chemistry , organic chemistry , chromatography
A planar‐chiral Cu/phosphaferrocene–oxazoline catalyst mediates intramolecular Kinugasa reactions to give tricyclic β‐lactams with good enantioselectivity. A variant of the process, in which a postulated enolate intermediate is intercepted with an electrophile in a transformation that generates two CC bonds, a CN bond, two new rings, a carbonyl group, and adjacent tertiary and quaternary stereocenters (see scheme), supports the proposed mechanism.