Copper-Catalyzed Asymmetric Oxidation of Sulfides

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• 作者：Graham E. O鈥橫ahony ; Alan Ford ; Anita R. Maguire
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：April 6, 2012
• 年：2012
• 卷：77
• 期：7
• 页码：3288-3296
• 全文大小：323K
• 年卷期：v.77,no.7(April 6, 2012)
• ISSN：1520-6904

文摘

Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure was examined, and the optimized conditions were then used to oxidize a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee).