ORGN 530 |
| Bakthan Singaram, C. Christopher Watts, Joelle Verhagen, and Brian Gallagher. Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High Street, Santa Cruz, CA 95064 |
| Ruthenium catalyzed transfer hydrogenation from isopropanol to ketones has proven to be an efficient method for the preparation of secondary alcohols. We have constructed optically active β-amino alcohols as a library of chiral auxiliaries based on the natural terpenes, limonene and carene. Naturally occurring terpenes such as limonene, carene and pinene are inexpensive compounds that are commercially available. A variety of these limonene and carene derived amino alcohols have been coordinated to (p-CymeneRuCl2)2 dimer complexes and screened for their catalytic abilities in the asymmetric transfer hydrogenation of a selection of ketones. This novel line of ruthenium-amino alcohol catalysts has yielded optically active secondary alcohols with up to 99% conversion and 71% enantiomeric excess. |
|
Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Wednesday, March 31, 2004 Anaheim Convention Center -- 303D, Oral
Division of Organic Chemistry |