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Direct Asymmetric anti-Mannich-Type Reactions Catalyzed by a Designed Amino Acid

Susumu Mitsumori, Haile Zhang, Paul Ha-Yeon Cheong, K. N. Houk, Fujie Tanaka and Carlos F. Barbas, III*

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

S. Mitsumori, H. Zhang, P. H.-Y. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas, III, J. Am. Chem. Soc., 2006, 128, 1040-1041.

DOI: 10.1021/ja056984f (free Supporting Information)


Abstract

(3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid as catalyst for Mannich-type reactions afforded anti-products in good yields with excellent diastereo- and enantioselectivities under mild conditions and low catalyst loadings.

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Key Words

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


ID: J48-Y2006-1400