Catalytic Dynamic Kinetic Resolutions with N‐Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β‐Lactones | Zendy

Cohen Daniel T. | Zendy; Eichman Chad C. | Zendy; Phillips Eric M. | Zendy; Zarefsky Emily R. | Zendy; Scheidt Karl A. | Zendy

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Catalytic Dynamic Kinetic Resolutions with N‐Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β‐Lactones

Author(s) -

Cohen Daniel T.,

Eichman Chad C.,

Phillips Eric M.,

Zarefsky Emily R.,

Scheidt Karl A.

Publication year - 2012

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.201203382

Subject(s) - catalysis , kinetic resolution , chemistry , kinetic energy , enantioselective synthesis , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , physics , quantum mechanics

New DKR type : An N‐heterocyclic carbene (NHC)‐catalyzed dynamic kinetic resolution of racemic α‐substituted β‐keto esters has been developed. This method relies on the epimerization of an NHC‐enol intermediate before subsequent aldol/acylation events. Highly substituted β‐lactones are produced in good yield with good to excellent selectivities (see scheme).

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