Asymmetric Aza-Mannich Reactions of Sulfinimines

Significance

Addition of enantiomerically pure sulfinimine anions to N-sulfonyl aldimines gave the addition product with excellent diastereoselectivity. The E-sulfonylimine is much more reactive than the Z-sulfonylimine, possibly due to the increased steric hinderance in the transition state of the Z-sulfonylimine. The single diastereoisomer obtained can be rationalized by the steric bulk and orientation of the tert-butylsulfonyl group.