APPROACHES TO COMPLEX CHIRAL QUATERNARY CARBON COMPOUNDS

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A program to continue studies on the use of chiral bicyclic lactams as valuable precursors to a variety of enantiomerically pure substances is presented. This study, which began in 1985, has shown that a variety of reactions performed on these chiral templates lead to efficient syntheses of quaternary carbon compounds found in many important biologically active materials. The present proposal will extend these studies to heretofore unreported chiral pyrrolidines, octalones, [3,3,0] bicyclic enones, spirocyclopentenones as well as useful cyclopropane amino acids, isoquinolines, amines, and others - all in high enantiomeric purity. As a demonstration of this asymmetric methodology, synthetic routes to a number of pharmaceutically significant systems are outlined.