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

Matthieu Hamel, Michel Vazeux, and Mihaela Gulea

Laboratoire de Chimie Moléculaire Et Thioorganique, Normandie University, ENSICAEN, UNICAEN, CNRS, Caen, France

 

E-mail: matthieu.hamel@cea.fr

Received: 19 March 2021  Accepted: 25 June 2021

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.

Keywords: Sulfenate ester; Sulfinate ester; Sulfoxide; Diastereoselective oxidation

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01759-9

 

Chemical Papers 75 (11) 6137–6143 (2021)

Thursday, June 20, 2024

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