A dual Lewis base activation strategy for enantioselective carbene-catalyzed annulations.

J Am Chem Soc

Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Silverman Hall, Evanston, Illinois 60208, USA.

Published: July 2013

A dual activation strategy integrating N-heterocyclic carbene (NHC) catalysis and a second Lewis base has been developed. NHC-bound homoenolate equivalents derived from α,β-unsaturated aldehydes combine with transient reactive o-quinone methides in an enantioselective formal [4 + 3] fashion to access 2-benzoxopinones. The overall approach provides a general blueprint for the integration of carbene catalysis with additional Lewis base activation modes.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3746556PMC
http://dx.doi.org/10.1021/ja405833mDOI Listing

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