A Facile and Efficient Approach to N-Protected-β-Sulfinylenamines via C-Sulfinylation of Enamides and Enecarbamates

A practical method has been developed for the C-sulfinylation of enamides and enecarbamates using sodium phenylsulfinate/methyltrichlorosilane (PhSO(2)Na/MeSiCl(3)) as the sulfinylating reagent and N,N-dimethylacetamide (DMAc) as the Lewis base promoter. which allows for the preparation of a variety of N-protected-beta-sulfinylenamines in high yields and good stereoselectivities. The Lewis base is found to be important for both the in situ generation of the active sulfinylating species (PhSOCl) and the sulfinylation step.