A recyclable fluorous (S)-pyrrolidine sulfonamide-promoted direct, highly enantioselective Michael addition ketones and aldehydes to nitroolefins in water

ORGN 149

Liansuo Zu, zls@unm.edu, Jian Wang, jxw01530@unm.edu, Hao Li, and Wei Wang, wwang@unm.edu. Department of Chemistry, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001
A recycle and reusable fluorous (S) pyrrolidine sulfonamide organocatalyst has been developed for promoting highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water. The organocatalyst is conveniently recovered from the reaction mixtures by fluorous solid-phase extraction and can be subsequently reused (up to 6 cycles) without a significant loss of catalytic activity and stereoselectivity.
 

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

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

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