Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids |
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Authors: | Chi Yonggui Guo Li Kopf Nathan A Gellman Samuel H |
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Institution: | Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA. |
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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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