Organocatalytic enantioselective cyclopropanations between alpha, beta-unsaturated aldehydes and bromomalonates

ORGN 597

Hexin Xie, xiehexin@unm.edu, Hao Li, haoli@unm.edu, Jian Wang, Liansuo Zu, zls@unm.edu, Wei Jiang, and Wei Wang, wwang@unm.edu. Department of Chemistry and Chemical Biology, University of New Mexico, 1 University of New Mexico, Albuquerque, NM 87131
The broad synthetic and biological utility of cyclopropanes has rendered them an attractive synthetic target in organic synthesis. The three-membered ring induced strain enables cyclopropanes to undergo a variety of ring-opening reactions. The first highly enantio- and diastereoselective domino Michael-alkylation reaction of alpha, beta-unsaturated aldehydes with bromomalonates has been developed. The process, efficiently catalyzed by chiral diphenylprolinol TMS ether, serves as a powerful approach to the preparation of synthetically and biologically significant cyclopropanes.
 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008