Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: Efficient access to γ2-amino acids

Yonggui Chi; Li Guo; Nathan A. Kopf; Samuel H. Gellman

doi:10.1021/ja800345r

Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: Efficient access to γ²-amino acids

Yonggui Chi, Li Guo, Nathan A. Kopf, Samuel H. Gellman

University of Wisconsin-Madison

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

155 Citations (Scopus)

Abstract

Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene catalyzed by (S)-diphenylprolinol silyl ether provides β-substituted-δ-nitroalcohols in nearly optically pure form (96-99% ee). The Michael adducts bear a single substituent adjacent to the carbonyl and can be efficiently converted to protected γ²-amino acids, which are essential for the systematic conformational studies of γ-peptide foldamers.

Original language	English
Pages (from-to)	5608-5609
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	17
DOIs	https://doi.org/10.1021/ja800345r
Publication status	Published - Apr 30 2008
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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AU - Gellman, Samuel H.

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Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: Efficient access to γ²-amino acids

Abstract

ASJC Scopus Subject Areas

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