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

Philippe Bertus* and Jan Szymoniak

*Laboratoire de Synthèse Organique, CNRS - UCO2M - Unité de chimie Moléculaire et Macromoléculaire, Université du Maine, Avenue O. Messiaen, F - 72085 Le Mans cedex 9, France, Email: Philippe.Bertusuniv-lemans.fr

P. Bertus, J. Szymoniak, J. Org. Chem., 2003, 68, 7133-7136.

DOI: 10.1021/jo034710+

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Abstract

The reaction of various aromatic nitriles and conjugated alkenenitriles with 1.1 equiv of Ti(OiPr)₄ and 2.2 equiv of EtMgBr followed by addition of a Lewis acid gave 1-arylcyclopropylamines and 1-alkenylcyclopropylamines in good yields.

see article for more examples

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New and easy route to primary cyclopropylamines from nitriles

P. Bertus, J. Szymoniak, Chem. Commun., 2001, 1792-1793.

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Key Words

Kulinkovich-Szymoniak Reaction, Cyclopropylamines, Alkylamines, Benzylamines, Allylamines

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ID: J42-Y2003-2190