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

Javier Izquierdo; Ane Orue; Karl A. Scheidt

doi:10.1021/ja405833m

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

Javier Izquierdo, Ane Orue, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

300 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	10634-10637
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	29
DOIs	https://doi.org/10.1021/ja405833m
State	Published - Jul 24 2013

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja405833m

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abstract = "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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AU - Scheidt, Karl A.

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Y1 - 2013/7/24

N2 - 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.

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

Abstract

ASJC Scopus subject areas

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CCDC 937894: Experimental Crystal Structure Determination

CCDC 937900: Experimental Crystal Structure Determination

CCDC 945180: Experimental Crystal Structure Determination

Cite this

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

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 937894: Experimental Crystal Structure Determination

CCDC 937900: Experimental Crystal Structure Determination

CCDC 945180: Experimental Crystal Structure Determination

Cite this