A Direct Synthesis of 1-Aryl- and 1-Alkenylcyclopropylamines from Aryl and Alkenyl Nitriles

Philippe Bertus* and Jan Szymoniak
CNRS UMR 6519, Ractions Slectives et Applications, Universit de Reims-Champagne-Ardenne, BP 1039, 51687 Reims Cedex 2, France philippe.bertus@univ-reims.fr
J. Org. Chem., 2003, 68 (18), pp 7133–7136
DOI: 10.1021/jo034710+
Publication Date (Web): August 13, 2003
Copyright © 2003 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.

Abstract

Abstract Image

The reaction of various aromatic nitriles with 1.1 equiv of Ti(Oi-Pr)4 and 2.2 equiv of EtMgBr followed by addition of a Lewis acid gave 1-aryl cyclopropylamines in 43−76% yields. Under similar conditions, conjugated alkenenitriles afford 1-alkenylcyclopropylamines (42−65%).

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History

  • Published In Issue September 05, 2003
  • Received May 26, 2003

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