Organocatalytic enantioselective direct vinylogous michael addition of α,β-unsaturated γ-butyrolactam to β-acyl acrylates and 1,2-diacylethylenes

Yi Ru Chen; Utpal Das; Meng Hsien Liu; Wenwei Lin

doi:10.1021/jo5027047

Organocatalytic enantioselective direct vinylogous michael addition of α,β-unsaturated γ-butyrolactam to β-acyl acrylates and 1,2-diacylethylenes

Yi Ru Chen, Utpal Das, Meng Hsien Liu, Wenwei Lin

Department of Chemistry

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

32 Citations (Scopus)

Abstract

A highly efficient Michael addition of α,β-unsaturated γ-butyrolactam to various β-acyl acrylates and ene-diones to provide synthetically useful compounds was developed. The products were obtained with high diastereo- and enantioselectivities (up to >25:1 dr and 99% ee) containing adjacent tertiary stereocenters.

Original language	English
Pages (from-to)	1985-1992
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	80
Issue number	3
DOIs	https://doi.org/10.1021/jo5027047
Publication status	Published - 2015 Feb 6

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo5027047

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abstract = "A highly efficient Michael addition of α,β-unsaturated γ-butyrolactam to various β-acyl acrylates and ene-diones to provide synthetically useful compounds was developed. The products were obtained with high diastereo- and enantioselectivities (up to >25:1 dr and 99% ee) containing adjacent tertiary stereocenters.",

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AU - Chen, Yi Ru

AU - Das, Utpal

AU - Liu, Meng Hsien

AU - Lin, Wenwei

PY - 2015/2/6

Y1 - 2015/2/6

N2 - A highly efficient Michael addition of α,β-unsaturated γ-butyrolactam to various β-acyl acrylates and ene-diones to provide synthetically useful compounds was developed. The products were obtained with high diastereo- and enantioselectivities (up to >25:1 dr and 99% ee) containing adjacent tertiary stereocenters.

AB - A highly efficient Michael addition of α,β-unsaturated γ-butyrolactam to various β-acyl acrylates and ene-diones to provide synthetically useful compounds was developed. The products were obtained with high diastereo- and enantioselectivities (up to >25:1 dr and 99% ee) containing adjacent tertiary stereocenters.

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