Access to Optically Pure Nitrogen Heterocycles Based on Hydrozirconation of Unsaturated Secondary Amines

M’hamed Ahari (1) , Antoine Joosten (1) , Jean-Luc Vasse (1) , Jan Szymoniak (1)

1 RSA - Réactions sélectives et applications

Optically active N-heterocycles with four-, five-, or six-membered rings can be prepared from unsaturated secondary amines, by using a one-pot hydrozirconation/iodination sequence as the key step. The presented method allows the preparation of 2-substituted pyrrolidines enantiomeric to those previously obtained from N-allyloxazolidines. The two approaches use the same reagents (allyl bromide and aldehydes) and the same (R)-2-phenyl­glycinol as the chiral inductor.

Domains: Chemical Sciences

M’hamed Ahari, Antoine Joosten, Jean-Luc Vasse, Jan Szymoniak. Access to Optically Pure Nitrogen Heterocycles Based on Hydrozirconation of Unsaturated Secondary Amines. Synthesis: Journal of Synthetic Organic Chemistry, 2008, 2008 (1), pp.61-68. ⟨10.1055/s-2007-990898⟩. ⟨hal-02548610⟩