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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, Email:

V. Gandon, P. Bertus, J. Szymoniak, Synthesis, 2002, 1115-1120.

DOI: 10.1055/s-2002-31962


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 such as 1-azaspirocyclic γ-lactams, pyrrolidines and azetidines.

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Key Words

Grignard reagents, benzylamines, azetidines, pyrrolidines, γ-lactams, imines, spiro compounds, zirconium

ID: J66-Y2002-1560