FEATUREARTICLE	Synthesis 2002: 1115-1120 DOI: 10.1055/s-2002-31962
© Georg Thieme Verlag Stuttgart · New York
Conversion of Imines into C,N-Dimagnesiated Compounds and Trapping with Electrophiles. One-Pot Access to 1-Azaspirocyclic Framework
Vincent Gandon, Philippe Bertus, Jan Szymoniak*
Réactions Sélectives et Applications, CNRS and Université de Reims, 51687 Reims Cedex 2, France Fax: +33(3)26913166; e-Mail: jan.szymoniak@univ-reims.fr;
Received 4 January 2002

Abstract

Under selected conditions, the Zr-catalyzed reaction of EtMgCl with imines produces C,N-dimagnesiated compounds, which can be further trapped with electrophiles. The overall transformation provides a new route to bifunctional or cyclic nitrogen-containing compounds. Particularly, 1-azaspirocyclic γ-lactams, pyrrolidines and azetidines can be obtained in this way.

Key Words

azetidines - Grignard reagents - imines - spiro compounds - zirconium