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

M’hamed Ahari; Antoine Joosten; Jean-Luc Vasse; Jan Szymoniak

doi:10.1055/s-2007-990898

PAPER

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

M’hamed Ahari, Antoine Joosten, Jean-Luc Vasse, Jan Szymoniak*
Réactions Sélectives et Applications, CNRS (UMR 6519) and , Université de Reims, 51687 Reims Cedex 2, France
Fax: +33(3)26913166; e-Mail: jan.szymoniak@univ-reims.fr;

Abstract

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Abstract

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.

Key words

hydrozirconation - nitrogen heterocycles - pyrrolidines - enantiomers

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Referenzen

References

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