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

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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