Formal diels-alder reactions of chalcones and formylcyclopropanes catalyzed by chiral n-heterocyclic carbenes

Hui Lv; Junming Mo; Xinqiang Fang; Yonggui Robin Chi

doi:10.1021/ol202250s

Formal diels-alder reactions of chalcones and formylcyclopropanes catalyzed by chiral n-heterocyclic carbenes

Hui Lv, Junming Mo, Xinqiang Fang, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

81 Citations (Scopus)

Abstract

Highly enantioselective (formal) hetero-Diels-Alder reactions between chalcones and formylcyclopropanes are disclosed. The challenging N-heterocyclic carbene (NHC)-bounded enolate intermediates from formylcyclopropanes were captured for new C-C bond forming reactions. The reaction products were obtained with high diastereo- and enantioselectivities and could be easily transformed to optically pure multisubstituted cyclohexane derivatives.

Original language	English
Pages (from-to)	5366-5369
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	19
DOIs	https://doi.org/10.1021/ol202250s
Publication status	Published - Oct 7 2011
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Highly enantioselective (formal) hetero-Diels-Alder reactions between chalcones and formylcyclopropanes are disclosed. The challenging N-heterocyclic carbene (NHC)-bounded enolate intermediates from formylcyclopropanes were captured for new C-C bond forming reactions. The reaction products were obtained with high diastereo- and enantioselectivities and could be easily transformed to optically pure multisubstituted cyclohexane derivatives.",

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AU - Lv, Hui

AU - Mo, Junming

AU - Fang, Xinqiang

AU - Chi, Yonggui Robin

PY - 2011/10/7

Y1 - 2011/10/7

N2 - Highly enantioselective (formal) hetero-Diels-Alder reactions between chalcones and formylcyclopropanes are disclosed. The challenging N-heterocyclic carbene (NHC)-bounded enolate intermediates from formylcyclopropanes were captured for new C-C bond forming reactions. The reaction products were obtained with high diastereo- and enantioselectivities and could be easily transformed to optically pure multisubstituted cyclohexane derivatives.

AB - Highly enantioselective (formal) hetero-Diels-Alder reactions between chalcones and formylcyclopropanes are disclosed. The challenging N-heterocyclic carbene (NHC)-bounded enolate intermediates from formylcyclopropanes were captured for new C-C bond forming reactions. The reaction products were obtained with high diastereo- and enantioselectivities and could be easily transformed to optically pure multisubstituted cyclohexane derivatives.

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Formal diels-alder reactions of chalcones and formylcyclopropanes catalyzed by chiral n-heterocyclic carbenes

Abstract

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