Enantioselective stetter reactions of enals and modified chalcones catalyzed by N-heterocyclic carbenes

Xinqiang Fang; Xingkuan Chen; Hui Lv; Yonggui Robin Chi

doi:10.1002/anie.201105812

Enantioselective stetter reactions of enals and modified chalcones catalyzed by N-heterocyclic carbenes

Xinqiang Fang, Xingkuan Chen, Hui Lv, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

105 Citations (Scopus)

Abstract

New trick for an old cat.: Triazolium-based N-heterocyclic carbenes (NHCs) catalyze the selective generation of acyl anion equivalents for the title reaction. The stereoelectronic properties of the enal-derived Breslow intermediates and the unique reactivity of the modified chalcones are crucial for the Stetter reactions to occur. EWG=electron- withdrawing group.

Original language	English
Pages (from-to)	11782-11785
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	49
DOIs	https://doi.org/10.1002/anie.201105812
Publication status	Published - Dec 2 2011
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

asymmetric catalysis
N-heterocyclic carbene
organocatalysis
Stetter reaction
synthetic methods

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10.1002/anie.201105812

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AU - Lv, Hui

AU - Chi, Yonggui Robin

PY - 2011/12/2

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AB - New trick for an old cat.: Triazolium-based N-heterocyclic carbenes (NHCs) catalyze the selective generation of acyl anion equivalents for the title reaction. The stereoelectronic properties of the enal-derived Breslow intermediates and the unique reactivity of the modified chalcones are crucial for the Stetter reactions to occur. EWG=electron- withdrawing group.

KW - asymmetric catalysis

KW - N-heterocyclic carbene

KW - organocatalysis

KW - Stetter reaction

KW - synthetic methods

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Enantioselective stetter reactions of enals and modified chalcones catalyzed by N-heterocyclic carbenes

Abstract

ASJC Scopus Subject Areas

Keywords

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