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anti-Selective Direct Asymmetric Mannich Reactions Catalyzed by Axially Chiral Amino Sulfonamide as an Organocatalyst

Taichi Kano, Yukako Yamaguchi, Osamu Tokuda and Keiji Maruoka*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan, Email: maruokakuchem.kyoto-u.ac.jp

T. Kano, Y. Yamaguchi, O. Tokuda, K. Maruoka, J. Am. Chem. Soc., 2005, 127, 16408-16409.

DOI: 10.1021/ja056008w (free Supporting Information)


Abstract

A direct highly anti-selective and enantioselective asymmetric Mannich reaction using a novel axially chiral amino trifluoromethanesulfonamide has been developed. Reactions between aldehydes and N-PMP-protected α-imino ethyl glyoxylate proceed smoothly to give β-amino aldehydes with high anti/syn ratio and enantioselectivity.

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Key Words

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


ID: J48-Y2005-2670