N-heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with alpha,beta-unsaturated acid fluorides

Sarah Ryan; Lisa Candish; David Lupton

doi:10.1021/ja111067j

N-heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with alpha,beta-unsaturated acid fluorides

Sarah Ryan, Lisa Candish, David Lupton

School of Chemistry

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

191 Citations (Scopus)

Abstract

Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with alpha,beta-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr > 20:1) while demonstrating a new type of reaction cascade exploiting alpha,beta-unsaturated acyl azoliums.

Original language	English
Pages (from-to)	4694 - 4697
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	13
DOIs	https://doi.org/10.1021/ja111067j
Publication status	Published - 2011

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10.1021/ja111067j

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abstract = "Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with alpha,beta-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr > 20:1) while demonstrating a new type of reaction cascade exploiting alpha,beta-unsaturated acyl azoliums.",

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AU - Candish, Lisa

AU - Lupton, David

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N2 - Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with alpha,beta-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr > 20:1) while demonstrating a new type of reaction cascade exploiting alpha,beta-unsaturated acyl azoliums.

AB - Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with alpha,beta-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr > 20:1) while demonstrating a new type of reaction cascade exploiting alpha,beta-unsaturated acyl azoliums.

UR - http://pubs.acs.org/doi/pdfplus/10.1021/ja111067j

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DO - 10.1021/ja111067j

M3 - Article

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 13

ER -

N-heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with alpha,beta-unsaturated acid fluorides

Abstract

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