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 Shū 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
Org. Lett., 2006, 8 (16), pp 3533–3536
DOI: 10.1021/ol0613012
Publication Date (Web): July 1, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, skobayas@mol.f.u-tokyo.ac.jp

Abstract

Abstract Image

The first example of the Lewis acid-catalyzed three-component direct-type Mannich reaction of simple aromatic and enolizable aliphatic aldehydes, secondary amines, and glycine derivatives is described. The procedure is highly atom economical and can be performed in a simple one-pot operation under mild conditions to afford a wide variety of synthetically important anti-α,β-diamino ester derivatives in high yields with high diastereoselectivities.

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History

  • Published In Issue August 03, 2006
  • Received May 28, 2006

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