SYNTHESIS AND CHARACTERIZATION OF CHIRAL OXAZOLIDINE-2-SELONES - A GENERAL ONE-STEP PROCEDURE FROM READILY AVAILABLE OXAZOLINES

The synthesis of a wide variety of chiral oxazolidine-2-selones from r eadily available 2-oxazolines has been accomplished in one step with y ields ranging from 82 to 98%. A mechanistic investigation of the forma tion of these selones has indicated the presence of intermediate anion s which have been characterized by C-13 and Se-77 NMR spectroscopy. X- ray crystallographic data suggest the chiral selones exists as dimeric pairs or networks linked by unusual selenium hydrogen bonds. These ch iral reagents exhibit extraordinary Se-77 chemical shift sensitivity a nd are useful fdr the detection and quantitation of chirality at remot ely disposed chiral centers.