Efficient Asymmetric Oxidation of Sulfides and Kinetic Resolution of Sulfoxides Catalyzed by a Vanadium−Salan System

Jiangtao Sun,† Chengjian Zhu,*†‡ Zhenya Dai,† Minghua Yang,† Yi Pan,† and Hongwen Hu†
School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China, and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China %cjzhu@netra.nju.edu.cn
J. Org. Chem., 2004, 69 (24), pp 8500–8503
DOI: 10.1021/jo040221d
Publication Date (Web): October 28, 2004
Copyright © 2004 American Chemical Society
†

 Nanjing University.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
‡

 Chinese Academy of Sciences.

Abstract

Abstract Image

The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by chiral vanadium−salan [N,N‘-alkyl bis(salicylamine)] complex. The salan ligand shows results superior in terms of reactivity and enantioselectivity to those of salen [N,N‘-alkylene bis(salicylideneimine)] analogue, and provides the sulfoxide with opposite configuration. The high enantioselectivity of this reaction is the direct result of the asymmetric oxidation. The efficient kinetic resolution of racemic sulfoxides catalyzed by the vanadium−salan system is also described.

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History

  • Published In Issue November 26, 2004
  • Received June 25, 2004

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