Diastereoselective oxidation of menthyl arenesulfenates to sulfinates and access to enantioenriched aryl methyl sulfoxides - Archive ouverte HAL Access content directly
Journal Articles Chemical Papers Year : 2021

Diastereoselective oxidation of menthyl arenesulfenates to sulfinates and access to enantioenriched aryl methyl sulfoxides

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Abstract

Three aryl methyl sulfoxides were prepared via the following sequence: synthesis of the menthyl arenesulfenate from the corresponding thiol, diastereoselective oxidation leading to the sulfinate, then reaction with a Grignard reagent. The aryl moiety was substituted with a methyl ester on the ortho position or a nitro group on the ortho or the para position. The sulfenate esters were obtained in fair to excellent yield (42-82%). Four different oxidizing agents were tested to obtain the corresponding sulfinate esters with diastereomeric excesses (de) ranging from 10 to 48%. After separation of the diastereomers and reaction with methyl Grignard reagent, two enantiopure sulfoxides, and one enantioenriched sulfoxide (32% ee) were obtained.
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cea-03334207 , version 1 (03-09-2021)

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Matthieu Hamel, Michel Vazeux, Mihaela Gulea. Diastereoselective oxidation of menthyl arenesulfenates to sulfinates and access to enantioenriched aryl methyl sulfoxides. Chemical Papers, 2021, 75 (11), pp.6137-6143. ⟨10.1007/s11696-021-01759-9⟩. ⟨cea-03334207⟩
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