(S)-Pyrrolidine sulfonamide and its recyclable version for promoting enantioselective organic reactions in organic and aqueous media

ORGN 21

Jian Wang, jxw01530@unm.edu, Hao Li, haoli@unm.edu, Liansuo Zu, zls@unm.edu, and Wei Wang, wwang@unm.edu. Department of Chemistry, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001
Recently, we have uncovered (S) pyrrolidine sulfonamide as a novel organocatalyst for catalyzing aldol, Mannich, Michael, alpha-sulfenylation, alpha-selenenylation, alpha-aminoxylation reactions with achieving excellent levels of enantioselectivities. In this presentation, we will highlight these results with a focus on the development of the first recycle and reusable fluorous (S) pyrrolidine sulfonamide for promoting highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water.
 

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