A method for the conversion of sulfoximines to sulfones: Application to polymer-bound sulfoximines and to the synthesis of chiral sulfones

Reaction of N-alkyl, N-aryl, and N-H sulfoximines with m-chloroperbenzoic a cid cleanly gives the corresponding sulfones in high yield. In the case of the cleavage of N-alkyl and N-arylsulfoximines, formation of the correspond ing nitroso compounds as the other reaction product was proven. Starting fr om enantio- and diastereopure sulfoximines, a number of chiral sulfones, in cluding the axially chiral sulfone 6 and the sulfonyl-functionalized homoal lylic alcohol 8, have been prepared. Reaction of the enantiopure sulfoximin e 30 with Merrifield resin gave the polymer-bound sulfoximine 32. Oxidative cleavage of 32 afforded the sulfone 16 in high yield. Deprotonation of the sulfoximine resin 32 and reaction of Li-32 with benzaldehyde and propanal furnished the beta-hydroxysulfoximine resins 33a and 33b, respectively. Oxi dative cleavage of 33a and 33b readily afforded the beta-hydroxy sulfones 1 4a and 14b, respectively.