Tuesday, July 1, 2008 - 7:50 PM
Amphitheater (Sheraton Burlington Hotel and Conference Center)
362

Catalytic, Asymmetric Reactions of Enolates

Michael A. Calter, Ryan M. Phillips, Jun Wang, Alexander Korotkov, and Na Li. Wesleyan University, Middletown, CT

We will describe several reactions of acidic carbonyl compounds with either carbonyl or enone electrophiles. Our research into this area began with the discovery of a catalytic, asymmetric version of the venerable Feist-Benary reaction. This reaction consists of an aldol reaction of an beta-dicarbonyl compound with an alpha-halocarbonyl compound, followed by an intramolecular SN2 reaction. We will describe the aromatization of the resulting products and the application of the aromatization products to the synthesis of glycinol. We will also describe our discovery of further versions of the asymmetric Feist-Benary reaction and the use of similar conditions to the development of an asymmetric Michael reaction between dicarbonyl compounds and enones. Finally, we will present preliminary results on the asymmetric self-aldol reactions of alpha-halocarbonyl compounds.