Highly stereoselective methylene transfers using S-ylide technologies

ORGN 725

David C. Forbes, dforbes@jaguar1.usouthal.edu, Sampada V. Bettigeri, sbettigeri@usouthal.edu, and Susanna C Pischek, scp403@jaguar1.usouthal.edu. Department of Chemistry, University of South Alabama, Chemistry Building (CHEM) , Room 223, Mobile, AL 36688-0002
Reaction of sulfur ylide with chiral non-racemic imine afforded the desired aziridine in excellent yield. Diastereomeric ratios of >95:5 were obtained. Both enantiomeric lines of the butanediacetal-protected chiral non-racemic sulfinyl imines were examined. The sulfur ylides were generated in situ upon thermal decarboxylation of carboxylmethyl betaine functionality. The enantiomeric pairs of D-mannitol with (S)-(-)-2-methyl-2-propane sulfinamide and ascorbic acid with (R)-(-)-2-methyl-2-propane sulfinamide resulted in the highest levels of diastereocontrol when performing aziridination reactions.