Asymmetric hydrogenation of homochiral vinylboronic esters and vinyloxazaborolidines under ambient conditions

ORGN 535

Bakthan Singaram, Soya Gamsey, and Kelly DeLaTorre. Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High Street, Santa Cruz, CA 95064

Novel homochiral vinyloxazaborolidines were synthesized and subsequently hydrogenated using Pd/C under ambient conditions to produce, after oxidation of the boronate group, enantiomerically enriched alcohols.  This study serves as the first example of asymmetric hydrogenation utilizing oxazaborolidines as chiral auxilaries.  Substrate syntheses and conformational studies will be described.

 

Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Wednesday, March 31, 2004 Anaheim Convention Center -- 303D, Oral

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004