Synthesis, deprotonation, and alkylation of S-allyl sulfoximines

Article abstract of DOI:10.1016/0040-4039(91)80202-H

N-Phenyl-S-(4-methylphenyl)-sulfoximidoyl chloride 1 reacts with allyltrimethylsilane in the presence of aluminum chloride to give benzothiazine 4 in fair yield along with a small amount of S-allyl sulfoximine 3a. On the other hand, 1 reacts with allyltributyltin to give the S-allyl sulfoximine 3a almost exclusively. This latter reaction appears to be general. The sulfoximine 3a is thermally stable and can be deprotonated smoothly with n-BuLi. The anion reacts regioselectively but not stereoselectively with simple alkylating agents. Reactions of the anion with selected aldehydes and enones proceeds with some regiocontrol and, with some exceptions, little stereocontrol.