Lewis Acid Activated Synthesis of Highly Substituted Cyclopentanes by the N‐Heterocyclic Carbene Catalyzed Addition of Homoenolate Equivalents to Unsaturated Ketoesters | Zendy

Cohen Daniel T. | Zendy; CardinalDavid Benoit | Zendy; Scheidt Karl A. | Zendy

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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.

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