Enantioselective One-Pot Three-Component Synthesis of Propargylamines

Alakesh Bisai and Vinod K. Singh*
Department of Chemistry, Indian Institute of Technology, Kanpur, India 208 016
Org. Lett., 2006, 8 (11), pp 2405–2408
DOI: 10.1021/ol060793f
Publication Date (Web): May 6, 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.

, vinodks@iitk.ac.in

Abstract

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A copper(I) complex of i-Pr-pybox-diPh has been found to be an efficient catalyst for an enantioselective one-pot three-component synthesis of propargylamines from aldehydes, amines, and alkynes. The reaction has been applied to a wide variety of aromatic aldehydes with excellent yields (up to 99%) and enantiomeric excesses (up to 99% ee). A transition-state model has been proposed to explain the stereochemical outcome of the reaction.

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History

  • Published In Issue May 25, 2006
  • Received April 3, 2006

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