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An efficient asymmetric oxidation of sulfides to sulfoxides

✍ Scribed by Philippe Pitchen; Henri B. Kagan

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
240 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

The Sharpless reagent (Ti(OiPr)4 t 1 mol eq. diethyl tartrate (DET) t 2 J-BuOOH) modified by addition of one mol eq. H20 gives a new homogeneous reagent which cleanly oxidizes sulfidesinto sulfoxides in dichloromethane. The best results were obtained for the stoichiometry Ti/DET/ H20/J-BuOOH = 1:2:1:2. The e.e. observed ranged from 4 to 93% with the highest beeing observed in the case of methyl p-tolyl sulfoxide. -Chiral sulfoxides are gaining considerable importance in synthesis as chiral synthonsforasym-1-4 metric C-C bond formation

πŸ“œ SIMILAR VOLUMES

Catalytic asymmetric oxidation of sulfid
Catalytic asymmetric oxidation of sulfides to sulfoxides using R-(+)-binaphthol
✍ Naoki Komatsu; Yoshiaki Nishibayashi; Toshio Sugita; Sakae Uemura πŸ“‚ Article πŸ“… 1992 πŸ› Elsevier Science 🌐 French βš– 173 KB

An asymmetric oxidation system using R-(+)-binaphthol as a chiral auxiliary catalyzes the oxidation of sulfides to chiral sulfoxides in good Β’nantiomeric excess ( up to 73% e.e. ) and in a high chemical yield. Although the chiral binaphthol derivatives have been used as an effective chiral auxiliar