Methylene transfers onto chiral N-sulfinyl imines

ORGN 724

David C. Forbes, dforbes@jaguar1.usouthal.edu1, Sampada V. Bettigeri, sbettigeri@usouthal.edu1, Sejal Amin1, Christie J. Bean1, Amanda M. Law, aml308@jaguar1.usouthal.edu1, and Robert A. Stockman2. (1) Department of Chemistry, University of South Alabama, Chemistry Building (CHEM) , Room 223, Mobile, AL 36688-0002, (2) School of Chemistry, Nottingham University, University Park, Nottingham, NG7 2RD, United Kingdom
Reaction of sulfur ylide with a series of aryl substituted chiral non-racemic sulfinyl imines afforded the corresponding aziridines in high yield and good stereoselection. The sulfur ylides were generated by the thermally induced decarboxylation of carboxymethylsulfonium betaines. A drop in the diastereomeric ratio was observed when going from electron deficient to electron releasing aryl substituted imines. S-Methylene aziridinations involving the decarboxylation of carboxymethylsulfonium betaine functionality compliments existing technologies with the advantages of the reaction protocol, levels of conversion and scope.
 

Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009