Novel optically active catalysts derived from limonene and carene for the asymmetric transfer hydrogenation of ketones by ruthenium (II) complexes

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.

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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