publication . Article . 2010

Enantioselective preparation of 1,3-dithiane 1-oxides by asymmetric oxidation of 1,3-dithianes bearing a chiral auxiliary

Y. WATANABE; Y. ONO; S. HAYASHI; Y. UENO; T. TORU;
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  • Published: 04 Aug 2010 Journal: Journal of the Chemical Society, Perkin Transactions 1 (issn: 0300-922X, eissn: 1364-5463, Copyright policy)
  • Publisher: Royal Society of Chemistry (RSC)
Abstract
Oxidation of 1,3-dithianes bearing a chiral auxiliary derived from (+) or (–)-camphor or diacetone D-(+)-glucose by the Sharpless reagent [Ti(OPri)4–diethyl L-(+)- or D-(–)-tartrate-ButOOH] affords, with high stereoselectivity, the monosulfoxides in good to excellent yields. Removal of the chiral auxiliary by base-catalysed hydrolysis yields (R)- and (S)-1,3-dithiane 1-oxides in high yields.
Subjects
free text keywords: Reagent, Chemistry, Photochemistry, Bearing (mechanical), law.invention, law, Enantioselective synthesis, Chiral auxiliary, chemistry.chemical_compound, Dithiane, Organic chemistry, Hydrolysis, Stereoselectivity
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publication . Article . 2010

Enantioselective preparation of 1,3-dithiane 1-oxides by asymmetric oxidation of 1,3-dithianes bearing a chiral auxiliary

Y. WATANABE; Y. ONO; S. HAYASHI; Y. UENO; T. TORU;