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Catalytic asymmetric oxidation of sulfides to sulfoxides using R-(+)-binaphthol

✍ Scribed by Naoki Komatsu; Yoshiaki Nishibayashi; Toshio Sugita; Sakae Uemura

Publisher: Elsevier Science
Year: 1992
Tongue: French
Weight: 173 KB
Volume: 33
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)79102-7

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✦ Synopsis

An asymmetric oxidation system using R-(+)-binaphthol as a chiral auxiliary catalyzes the oxidation of sulfides to chiral sulfoxides in good ¢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 auxiliary in many asymmetric reactions because of its extraordinary chiral recognition properties, 1 theywere almost uneffecdve ligands for Sharpless epoxidadon. 2 it has been described that the ester or amide oxygens were required at both ends of a diol ligand for a good enandoselccdvity to be obtained in the epoxidadon. Recently, however, several

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