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Catalysis of 3-Pyrrolidinecarboxylic Acid and Related Pyrrolidine Derivatives in Enantioselective anti-Mannich-Type Reactions: Importance of the 3-Acid Group on Pyrrolidine for Stereocontrol

Haile Zhang, Susumu Mitsumori, Naoto Utsumi, Masanori Imai, Noemi Garcia-Delgado, Maria Mifsud, Klaus Albertshofer, 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: ftanakascripps.edu, carlosscripps.edu

H. Zhang, S. Mitsumori, N. Utsumi, M. Imia, N. Garcia-Delgado, M. Mifsud, K. Albertshofer, P. H.-Y. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas, III, J. Am. Chem. Soc., 2008, 130, 875-886.

DOI: 10.1021/ja074907+ (free Supporting Information)


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Abstract

Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the Mannich-type reactions of aldehydes with α-imino esters under mild conditions and afforded anti-Mannich products with high diastereo- and enantioselectivities.

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Key Words

Mannich Reaction, Amino Acids, Organocatalysis


ID: J48-Y2008-0200