Intermolecular and intramolecular Pauson-Khand reactions of cyclopropenes

ORGN 146

Mahesh K. Pallerla and Joseph M. Fox. Department of Chemistry and Biochemistry, University of Delaware, 263 Brown Lab, Newark, DE 19716
The Pauson-Khand (PK) reaction is a regio and stereo selective means to synthesize substituted cylopentenones. Although is has been long known that strained alkenes are excellent substrates for PK reactions, PK reactions of cyclopropenes have not been studied extensively. We have recently developed general reactions for obtaining a variety of chiral cyclopropenes in enantiomerically pure form. Herein, we present successful high yielding PK reaction of chiral cyclopropenes. The reactions are regio and stereoselective, and the chirality of the cyclopropene can efficiently be transferred to the PK products. Remarkably, tetrasubstituted alkenes react efficiently.

This poster will present our progress toward devloping general reaction conditions for the cyclopropene PK reactions, as well as our progress toward the asymmetric synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740)

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004