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. 2008 Apr 30;130(17):5608-9.
doi: 10.1021/ja800345r. Epub 2008 Apr 4.

Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids

Yonggui Chi  1 , Li Guo, Nathan A Kopf, Samuel H Gellman
Affiliations

Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids

Yonggui Chi et al. J Am Chem Soc. .

Abstract

Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene catalyzed by (S)-diphenylprolinol silyl ether provides beta-substituted-delta-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 gamma2-amino acids, which are essential for the systematic conformational studies of gamma-peptide foldamers.

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