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