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Catalytic Silicon-Mediated Carbon-Carbon Bond-Forming Reactions of Unactivated Amides

Shū Kobayashi*, Hiroshi Kiyohara and Miyuki Yamaguchi

*Department of Chemistry, School of Science, and Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan, Email: shu_kobayashichem.s.u-tokyo.ac.jp

S. Kobayashi, H. Kiyohara, M. Yamaguchi, J. Am. Chem. Soc., 2011, 133, 708-711.

DOI: 10.1021/ja108764d (free Supporting Information)



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Abstract

In the presence of catalytic amounts of trialkylsilyl triflate and triethylamine, unactivated amides react with imines to afford the corresponding Mannich-type adducts in high yields with high anti selectivities. It is noteworthy that unactivated simple amides bearing α-protons that are less acidic than those of ketones and aldehydes can be successfully used in catalytic direct-type addition reactions.


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proposed catalytic cycle



Key Words

Mannich Reaction, β-amino amides


ID: J48-Y2011-0210