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Lewis Acid Activated Synthesis of Highly Substituted Cyclopentanes by the N‐Heterocyclic Carbene Catalyzed Addition of Homoenolate Equivalents to Unsaturated Ketoesters
Author(s) -
Cohen Daniel T.,
CardinalDavid Benoit,
Scheidt Karl A.
Publication year - 2011
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.201005908
Subject(s) - cyclopentanes , carbene , stereocenter , lewis acids and bases , catalysis , chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis
A great team : Cyclopentanes with four contiguous stereogenic centers were assembled with excellent diastereo‐ and enantioselectivity from simple β,γ‐unsaturated α‐ketoesters and enals in a reaction catalyzed by an N‐heterocyclic carbene (NHC) and mediated by a titanium(IV) Lewis acid (see scheme). The presence of a Lewis acid was essential for the desired transformation to occur.