A Dual Lewis Base Activation Strategy for Enantioselective Carbene-Catalyzed Annulations

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 acces...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 135; no. 29; pp. 10634 - 10637
Main Authors Izquierdo, Javier, Orue, Ane, Scheidt, Karl A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.07.2013
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Benzene Derivatives - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Indolequinones - chemistry
Lewis Bases - chemistry
Methane - analogs & derivatives
Methane - chemistry
Physical Sciences
Science & Technology
ASYMMETRIC CATALYSIS
BENZAZEPINONE
KETONES
N-HETEROCYCLIC CARBENE
COOPERATIVE CATALYSIS
ACIDS
ALPHA,BETA-UNSATURATED ALDEHYDES
CONJUGATE UMPOLUNG
O-QUINONE METHIDES
ENALS
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja405833m