Novel L-prolinamide derivatives as a highly efficient catalyst for direct aldol reaction

ORGN 109

Sampak Samanta, sampak.samanta@utsa.edu, Rajasekhar Dodda, and Cong-Gui Zhao. Department of Chemistry, University of Texas at San Antonio, 6900 N Loop 1604 W, San Antonio, TX 78249
We have designed and synthesized a family of organocatalysts based on hydrogen bonding ability of remote amide hydrogen atom to catalyze asymmetric aldol reaction of ketones and aldehydes. The corresponding â-hydroxy ketones have been obtained with excellent enantioselectivities (up to >99% ee) with 2-10 mol% loading of these catalysts. The dependence of the reactivity and enantioselectivity of these catalysts on the hydrogen bonds formed in the TS will be discussed.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006