Highly reactive organocatalyst for the asymmetric aldol process

ORGN 30

Eric Lacoste, lacoste.eric@gmail.com1, Jean-Marc Vincent, jm.vincent@lcoo.u-bordeaux1.fr2, and Yannick Landais2. (1) Department of Chemistry, current address - University of Washington, Box 351700, Seattle, WA 98195-1700, (2) Laboratoire de Chimie Organique et Organometallique, UMR CNRS 5802, 351 Cours de la Libération, Bat A12, Université Bordeaux 1, 33400 Talence, France
Organocatalysis is a very active research area and new methodologies are actively developed. In order to expand the structural diversity of pyrrolidine-based catalysts, we recently prepared in a single step from commercial compounds, the new benzoimidazole-pyrrolidine (BiP). The BiP/TFA association is highly efficient for the enantioselective aldol reaction, as depicted below. The scope and limitations of this system will be discussed, with special emphasis on the reaction mechanism and the role of the acid.

 

Asymmetric Reactions and Syntheses
8:00 AM-12:20 PM, Sunday, 10 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

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