ArticleBeilstein journal of organic chemistry2026
Circumventing Mukaiyama oxidation: selective S-O bond formation via sulfenamide-alcohol coupling.
Article in Beilstein journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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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 sulfilimines with up to 93% ee. These results demonstrate the potential of sulfinimidate esters as versatile intermediates for enantioselective S-C bond formation under mild and metal-free conditions.
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