THE SYNTHESIS OF A WIDE VARIETY OF CHIRAL OXAZOLIDIN-2-SELONES FROM READILY AVAILABLE 2-OXAZOLINES HAS BEEN ACCOMPLISHED IN ONE STEP WITH YIELDS RANGING FROM 82-98%. 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. THESE RESULTS UNDERSCORE THE IMPORTANCE OF CHIRAL SELONES AS A NEW GENERATION OF CHIRAL AUXILIARY REAGENTS WHICH HAVE DOUBLED THE LIMITS OF DETECTION OF THE AGENTS CURRENTLY EMPLOYED. THEY ARE COMPLEMENTARY TO MOST OF THE EXISTING CDA'S IN THAT THEY ARE USEFUL WITH A VARIETY OF DIFFERENT FUNCTIONAL GROUPS, INCLUDING CARBOXYLIC ACIDS. OVERALL, THESE DATA INDICATE THAT THE CONSTRUCTION OF A NUMBER OF ENANTIOMERICALLY PURE SELONE CDA'S CAN BE ACCOMPLISHED IN 2 STEPS FROM COMMERCIALLY AVAILABLE CHIRAL 2-AMINO-ALCOHOLS IN HIGH YIELD AND IN BULK. USE OF HAZARDOUS MATERIALS AND THE NEED FOR PRIOR GENERATION OF A CARBONYL/SELONE EXCHANGE REAGENT ARE NOT INCLUDED IN THIS SYNTHESIS. MOREOVER, X-RAY STUDIES HAVE UNCOVERED AN UNUSUAL SELENIUM-HYDROGEN BONDING EVENT IN THE SOLID STATE FOR THIS CLASS OF SELONES. WE HAVE DEMONSTRATED THE ADVANTAGES OF USING 77SE NMR SPECTROSCOPY IN DETECTING SMALL NUANCES IN THE CHEMICAL AND ELECTRONIC ENVIRONMENT OF THE SELENIUM NUCLEUS. THIS SENSITIVITY IS EVEN GREATER IN COMPOUNDS CONTAINING CARBON-SELENIUM DOUBLE BONDS. STUDIES ARE ONGOING TO EXPLOIT THIS SENSITIVITY VIA NMR SPECTROSCOPY AND TO INCREASE THE NATURE AND NUMBER OF FUNCTIONAL GROUPS WHICH CAN BE COUPLED AND SUBSEQUENTLY EVALUATED BY 77SE NMR SPECTROSCOPY WITH THIS NEW CLASS OF CHIRAL CDA'S.
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