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.