Stereoselective preparation of b-hydroxy-b-trifluoromethyl ketones and a,b-dihydroxy-b-trifluoromethyl ketones, using chiral (L) proline as a catalyst

ORGN 49

G. K. Surya Prakash1, Chiradeep Panja1, Mihirbaran Mandal1, Hiriyakkanavar Ila2, and George A. Olah1. (1) Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, (2) Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India, Kanpur, India

Stereoselective aldol condensation of 1,1,1-trifluoromethyl ketones was carried out with acetone and hydroxyacetone, using chiral (L) proline as a catalyst. Good to excellent chemical yields (75-98 %) were obtained. Moderate enantioselectivities were realized in the reactions with acetone. Good regioselectivities and diastereoselectivities were observed for the reactions with hydroxyacetone.

New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics 8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster Division of Organic Chemistry The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004