Stereoselective radical addition of an acetal to sterically tuned enantiomerically pure N-sulfinyl imines

Abstract

Enantiomerically enriched sulfonamides were synthesized by the radical addition of an acetal to enantiomerically pure N-sulfinyl imines using dimethylzinc-air and boron trifluoride diethyl etherate. Higher levels of stereocontrol were observed by using a mesitylenesulfinyl group. Furthermore, an amine and an amino alcohol with high enantiomeric purity were obtainable from the sulfonamide product. © 2010 Pharmaceutical Society of Japan.