Circumventing Mukaiyama oxidation: selective S-O bond formation via sulfenamide-alcohol coupling.

ABSTRACT: A selective and efficient method for the synthesis of sulfinimidate esters via an NBS-promoted oxidative coupling of sulfenamides with alcohols has been developed. This operationally simple, metal-free protocol uses inexpensive and readily available reagents, operates under mild conditions, exhibits a broad substrate scope and high chemoselectivity, and clearly distinguishes itself from classical Mukaiyama-type oxidations. The reaction is readily scalable to gram quantities and is applicable to late-stage functionalization of complex alcohols, including bioactive molecules such as RU58841. Moreover, chiral alcohols such as ʟ-menthol are well tolerated, affording diastereomeric sulfinimidate esters that can undergo stereospecific Grignard substitutions to furnish enantioenriched sulfilimine

SUBMITTER: Huang G 

PROVIDER: S-EPMC12834055 | biostudies-literature | 2026

REPOSITORIES: biostudies-literature