Enantioselective Diels-Alder reactions of enals and alkylidene diketones catalyzed by N-heterocyclic carbenes

Xinqiang Fang; Xingkuan Chen; Yonggui Robin Chi

doi:10.1021/ol201917u

Enantioselective Diels-Alder reactions of enals and alkylidene diketones catalyzed by N-heterocyclic carbenes

Xinqiang Fang, Xingkuan Chen, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

117 Citations (Scopus)

Abstract

An electron-withdrawing group was introduced to the α-position of chalcones, and the resulting alkylidene diketones showed new reactivities with enals under the catalysis of N-heterocyclic carbenes (NHCs). Selective activation of enals affords enolate equivalents that undergo highly enantioselective intermolecular Diels-Alder reactions with the alkylidene diketones. No products that might have resulted from typical homoenolate pathways were observed.

Original language	English
Pages (from-to)	4708-4711
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	17
DOIs	https://doi.org/10.1021/ol201917u
Publication status	Published - Sept 2 2011
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "An electron-withdrawing group was introduced to the α-position of chalcones, and the resulting alkylidene diketones showed new reactivities with enals under the catalysis of N-heterocyclic carbenes (NHCs). Selective activation of enals affords enolate equivalents that undergo highly enantioselective intermolecular Diels-Alder reactions with the alkylidene diketones. No products that might have resulted from typical homoenolate pathways were observed.",

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Y1 - 2011/9/2

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AB - An electron-withdrawing group was introduced to the α-position of chalcones, and the resulting alkylidene diketones showed new reactivities with enals under the catalysis of N-heterocyclic carbenes (NHCs). Selective activation of enals affords enolate equivalents that undergo highly enantioselective intermolecular Diels-Alder reactions with the alkylidene diketones. No products that might have resulted from typical homoenolate pathways were observed.

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Enantioselective Diels-Alder reactions of enals and alkylidene diketones catalyzed by N-heterocyclic carbenes

Abstract

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