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Direct-Type Catalytic Three-Component Mannich Reactions Leading to an Efficient Synthesis of α,β-Diamino Acid Derivatives

Matthew M. Salter, Jun Kobayashi, Yusuke Shimizu and Shu Kobayashi*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Corporation (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: skobayasmol.f.u-tokyo.ac.jp

M. M. Salter, J. Kobayashi, Y. Shimizu, S. Kobayashi, Org. Lett., 2006, 8, 3533-3536.

DOI: 10.1021/ol0613012 (free Supporting Information)


Abstract

A Lewis acid-catalyzed three-component, mild, highly atom econocial, direct-type Mannich reaction of simple aromatic and enolizable aliphatic aldehydes, secondary amines, and glycine derivatives affords various synthetically important anti-α,β-diamino ester derivatives in high yields with high diastereoselectivities.

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Key Words

1,2-Diamines, α-Amino Acid Derivatives, Multicomponent Reactions, Mannich Reaction, Sodium Cyanoborohydride


ID: J54-Y2006-2390