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Enantioselective Organocatalytic Michael Addition of Aldehydes to Nitroethylene: Efficient Access to γ2-Amino Acids

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

*Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, Email: gellmanchem.wisc.edu

Y. Chi, L. Guo, N. A. Kopf, S. H. Gellman, J. Am. Chem. Soc., 2008, 130, 5048-5049.

DOI: 10.1021/ja800345r


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. The Michael adducts bear a single substituent adjacent to the carbonyl and can be efficiently converted to protected γ2-amino acids.

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Key Words

Nitro Compounds, Organocatalysis


ID: J48-Y2008-1070