N'-DIMETHYLCYCLOHEXYL-1,2-DIAZASELENOPHOSPHOLIDINE AS A CHIRAL DERIVATIZING AGENT FOR THE EVALUATION OF CHIRAL ALCOHOLS

Previously, a diazaphospholidine has been synthesized and evaluated as a chiral derivatizing reagent for the determination of the optical pu rity of chiral alcohols via P-31 NMR spectroscopy (Alexakis et al., J. Org. Chem. 57:1224-1237, 1992). Our laboratory is interested in the a dvantageous and practical applications of Se-77 NMR spectroscopic stud ies in many facets of chemistry and biochemistry. To this end we have used this diazaphospholidine as a starting point and have investigated chiral alcohols coupled to an optically pure diazaselenophospholidine . The diastereomers formed were then evaluated by Se-77 NMR spectrosco py, and these results were compared to the P-31 NMR results published by Alexakis and co-workers. It was found that addition of the Se atom produced diastereomers that were air stable and, in many cases, the in dividual diastereomers could be distinguished by Se-77 NMR spectroscop y. Preliminary results indicate that the Se-77 nucleus is somewhat mor e sensitive to remotely disposed chiral centers than is the P-31 nucle us. Furthermore, because of their stability, these compounds do not re adily decompose and can, therefore, be studied by a variety of chromat ographic and spectroscopic techniques. (C) 1994 Wiley-Liss, Inc.