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Enantioselective oxidation of sulfides catalyzed by titanium complexes of 1,2-diarylethane-1,2-diols: Effect of the aryl substitution

✍ Scribed by Stefano Superchi; Patrizia Scafato; Lina Restaino; Carlo Rosini

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
93 KB
Volume
20
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

The effects of the substitution on the aryl moiety on the asymmetric oxidation of sulfides mediated by Ti‐complexes of chiral 1,2‐diarylethane‐1,2‐diols were investigated. The substitution of the aryl ring of the diol with both EWG and EDG substituents generally decreased the enantioselectivity with respect to the use of unsubstituted 1,2‐diphenylethane‐1,2‐diol (1a). Only in the presence of 1,2‐di(4‐t‐butyl)phenyl‐1,2‐diol (1g) were higher ee's obtained with aryl methyl and aryl benzyl sulfides affording ee's up to 90 and 99%, respectively. Lower ee's were achieved with larger naphthyl and aryl alkyl sulfides. Contrary to the other Ti‐alcoholates used in the oxidation of sulfides, the Ti‐complex of diol 1g was soluble in hexane, allowing us to perform the process with high enantioselectivity in this solvent, with great environmental advantages over the commonly used chlorinated solvents. Chirality, 2008. © 2008 Wiley‐Liss, Inc.

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Catalytic asymmetric oxidation of aryl m
Catalytic asymmetric oxidation of aryl methyl sulfides mediated by a (S,S)-1,2-diphenylethan-1,2-diol/titanium/water complex
✍ Stefano Superchi; Carlo Rosini 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 238 KB

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