cis-Enals in N-heterocyclic carbene-catalyzed reactions: Distinct stereoselectivity and reactivity

Xingkuan Chen; Xinqiang Fang; Yonggui Robin Chi

doi:10.1039/c3sc50666e

cis-Enals in N-heterocyclic carbene-catalyzed reactions: Distinct stereoselectivity and reactivity

Xingkuan Chen, Xinqiang Fang, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

61 Citations (Scopus)

Abstract

The first successful generation of cis-homoenolate equivalents from cis-enals under the catalysis of N-heterocyclic carbenes (NHCs) has been realized. The cis-homoenolate intermediates undergo effective reactions with α,β-unsaturated imines to afford chiral cyclic ketone products. Compared to the trans-enals, cis-enals show different stereoselectivities and new reactivity patterns.

Original language	English
Pages (from-to)	2613-2618
Number of pages	6
Journal	Chemical Science
Volume	4
Issue number	6
DOIs	https://doi.org/10.1039/c3sc50666e
Publication status	Published - May 7 2013
Externally published	Yes

ASJC Scopus Subject Areas

General Chemistry

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abstract = "The first successful generation of cis-homoenolate equivalents from cis-enals under the catalysis of N-heterocyclic carbenes (NHCs) has been realized. The cis-homoenolate intermediates undergo effective reactions with α,β-unsaturated imines to afford chiral cyclic ketone products. Compared to the trans-enals, cis-enals show different stereoselectivities and new reactivity patterns.",

author = "Xingkuan Chen and Xinqiang Fang and {Robin Chi}, Yonggui",

year = "2013",

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T2 - Distinct stereoselectivity and reactivity

AU - Chen, Xingkuan

AU - Fang, Xinqiang

AU - Robin Chi, Yonggui

PY - 2013/5/7

Y1 - 2013/5/7

N2 - The first successful generation of cis-homoenolate equivalents from cis-enals under the catalysis of N-heterocyclic carbenes (NHCs) has been realized. The cis-homoenolate intermediates undergo effective reactions with α,β-unsaturated imines to afford chiral cyclic ketone products. Compared to the trans-enals, cis-enals show different stereoselectivities and new reactivity patterns.

AB - The first successful generation of cis-homoenolate equivalents from cis-enals under the catalysis of N-heterocyclic carbenes (NHCs) has been realized. The cis-homoenolate intermediates undergo effective reactions with α,β-unsaturated imines to afford chiral cyclic ketone products. Compared to the trans-enals, cis-enals show different stereoselectivities and new reactivity patterns.

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cis-Enals in N-heterocyclic carbene-catalyzed reactions: Distinct stereoselectivity and reactivity

Abstract

ASJC Scopus Subject Areas

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