Chiral pyrrolidine sulfonamide-promoted direct, highly enantio- and diastereoselective Michael addition of ketones to enones

ORGN 79

Jian Wang, Hao Li, Liansuo Zu, and Wei Wang, wwang@unm.edu. Department of Chemistry, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001
Michael addition reactions are powerful tools for the generation of new C-C bonds as part of synthetic routes for the preparation of complex organic targets. Recently, organocatalyzed asymmetric version of the processes has been intensively studied. However, direct, organocatalytic conjugate addition of ketones to enones remains challenging and studies probing this issue have not yet been reported. In this presentation, we would like to describe the results of an investigation, which has led to the development of the first method for carrying out highly enantioselective, organocatalytic Michael addition reactions of ketones with alpha,beta-unsaturated ketones by using a chiral pyrrolidine sulfonamide.