N-Heterocyclic carbene-catalyzed enantioselective annulations: A dual activation strategy for a formal [4+2] addition for dihydrocoumarins

Anna Lee; Karl A. Scheidt

doi:10.1039/c4cc09590a

N-Heterocyclic carbene-catalyzed enantioselective annulations: A dual activation strategy for a formal [4+2] addition for dihydrocoumarins

Anna Lee, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

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

101 Scopus citations

Abstract

A highly efficient asymmetric formal [4+2] annulation for the synthesis of dihydrocoumarins has been developed via an in situ activated NHC catalysis. Both electrophilic and nucleophilic species are generated in situ simultaneously whereby acyl imidazoles facilitated rapid formation of an NHC-enolate intermediate to afford the [4+2] dihydrocoumarin adducts.

Original language	English (US)
Pages (from-to)	3407-3410
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	16
DOIs	https://doi.org/10.1039/c4cc09590a
State	Published - Feb 25 2015

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Ceramics and Composites
Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
Chemistry(all)
Catalysis

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abstract = "A highly efficient asymmetric formal [4+2] annulation for the synthesis of dihydrocoumarins has been developed via an in situ activated NHC catalysis. Both electrophilic and nucleophilic species are generated in situ simultaneously whereby acyl imidazoles facilitated rapid formation of an NHC-enolate intermediate to afford the [4+2] dihydrocoumarin adducts.",

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AB - A highly efficient asymmetric formal [4+2] annulation for the synthesis of dihydrocoumarins has been developed via an in situ activated NHC catalysis. Both electrophilic and nucleophilic species are generated in situ simultaneously whereby acyl imidazoles facilitated rapid formation of an NHC-enolate intermediate to afford the [4+2] dihydrocoumarin adducts.

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N-Heterocyclic carbene-catalyzed enantioselective annulations: A dual activation strategy for a formal [4+2] addition for dihydrocoumarins

Abstract

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