Synthesis and Characterization of Chiral Oxazolidine-2-selones: A General One-Step Procedure from Readily Available Oxazolines

Article abstract of DOI:10.1021/jo00096a048

The synthesis of a wide variety of chiral oxazolidine-2-selones from readily available 2-oxazolines has been accomplished in one step with yields ranging from 82 to 98percent.A mechanistic investigation of the formation of these selones has indicated the presence of intermediate anions which have been characterized by 13C and 77Se NMR spectroscopy.X-ray crystallographic data suggest the chiral selones exists as dimeric pairs or networks linked by unusual selenium hydrogen bonds.These chiral reagents exhibit extraordinary 77Se chemical shift sensitivity and are useful for the detection and quantitation of chirality at remotely disposed chiral centers.