From isoxazolidines to tetrahydro-1,3-oxazines for the synthesis of chiral pyrrolidines??

RSC Advances Pub Date: 2012-09-17 DOI: 10.1039/C2RA22110A

Abstract

A novel approach for the synthesis of chiral tetrasubstituted pyrrolidines has been developed. The rearrangement of isoxazolidines into tetrahydro-1,3-oxazines using reactive organic bromides is herein described for the first time. The subsequent opening reaction of these tetrahydro-1,3-oxazines with nucleophiles probes the usefulness of the method for the synthesis of biologically active compounds.

Graphical abstract: From isoxazolidines to tetrahydro-1,3-oxazines for the synthesis of chiral pyrrolidines
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