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A Highly Enantioselective Route to Either Enantiomer of Both α- and β-Amino Acid Derivatives

Armando Córdova, Wolfgang Notz, Guofu Zhong, Juan M. Betancort and Carlos F. Barbas III*

*The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Rd., La Jolla, California 92037, Email: carlosscripps.edu

A. Cordova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, J. Am. Chem. Soc., 2002, 124, 1866-1867.

DOI: 10.1021/ja017833p (free Supporting Information)


Abstract

This is the first report concerning the use of unmodified aldehydes as a nucleophiles in direct catalytic asymmetric Mannich reactions.

Proline-catalyzed Mannich-type reactions of N-PMP-protected α-imino ethyl glyoxylate with a variety of unmodified aliphatic aldehydes provided functionalized α-amino acids in high yields with excellent enantioselectivities. The diastereoselectivity of the reaction increased with the bulkiness of the substituents of the aldehyde donor.

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Key Words

Organocatalysis, Mannich Reaction, β-Amino Aldehydes, α-Amino Acids


ID: J48-Y2002-1070