publication . Article . 2010

Asymmetric Oxidation of 1,3‐Dithianes to 1,3‐Dithiane 1‐Oxides.

Yoshihiko Watanabe; Yohjiro Ohno; Yoshio Ueno; Takeshi Toru;
Open Access English
  • Published: 21 Jun 2010 Journal: Journal of the Chemical Society. Perkin transactions 1 : organic and bio-organic chemistry., volume 1,998, issue 6, pages 1,087-1,093 (issn: 0300922x, Copyright policy)
  • Publisher: Royal Society of Chemistry
Abstract
Oxidation of 2-(1-hydroxy-1-methylethyl)-1,3-dithiane with the Sharpless reagent has been examined under various reaction conditions. Oxidation of 2-(1-hydroxy-1-methylethyl)-1,3-dithiane with Ti(OPri)4-diethyl L-(+)-tartrate-tert-butyl hydroperoxide (1:2:1.5) in CH2Cl2 in the presence of 4 A molecular sieves gives (1S,2S)-2-(1-hydroxy-1-methylethyl)-1,3-dithiane 1-oxide with high trans selectivity and with moderate enantioselectivity. The enantioselectivity depends upon the substituent at the 2-position of the 1,3-dithiane. Oxidation of 2-(1-methoxy-1-methylethyl)- and 2-(1-acetoxy-1-methylethyl)-1,3-dithiane gives (1S,2S)-2-(1-methoxy-1-methylethyl)- and (1R,2...
Subjects
free text keywords: Dithiane, chemistry.chemical_compound, chemistry, Organic chemistry, Selectivity, Substituent, Reaction conditions, Photochemistry, Molecular sieve, Reagent
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publication . Article . 2010

Asymmetric Oxidation of 1,3‐Dithianes to 1,3‐Dithiane 1‐Oxides.

Yoshihiko Watanabe; Yohjiro Ohno; Yoshio Ueno; Takeshi Toru;