Applications of a highly enantioselective sulfur-ylide in epoxidation reactions

ORGN 351

Catherine P Tubb, cpt27@cam.ac.uk, Department of Chemistry, University of Cambridge, Lensfield Road, Lensfield Rd., Cambridge, CB21EW, United Kingdom and Jonathan M Goodman, J.M.Goodman@ch.cam.ac.uk, Unilever Centre for Molecular Science Informatics, Cambridge University, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
We have established the use of enantiomerically pure tricyclic C2 sulfide 1 (derived in 3 steps in excellent yield from D-mannitol) in epoxidation reactions. Its enantiomer 2 can now be prepared from dimethyl-L-tartrate. When used in a one-pot sulfur ylide mediated epoxidation reactions between 94-96% enantiomeric excess were obtained for the preparation of stilbene oxide.

Extension of the methodology has been used in the epoxidation of allylic, aliphatic and activated aldehydes and ketones. The scope of these epoxidation reactions will be described.

 

New Reactions and Methodology, Bioorganic Chemistry, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006