Synlett 2002(1): 0161-0163
DOI: 10.1055/s-2002-19361
LETTER
© Georg Thieme Verlag Stuttgart · New York

Vanadium-catalyzed Enantioselective Sulfoxidation of Methyl Aryl Sulfides with Hydrogen Peroxide as Terminal Oxidant

Chisa Ohta, Hideki Shimizu, Akiko Kondo, Tsutomu Katsuki*
Department of Chemistry, Faculty of Science, Graduate School, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
Fax: +81(92)6422607; e-Mail: katsuscc@mbox.nc.kyushu-u.ac.jp;
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Publikationsverlauf

Received 5 November 2001
Publikationsdatum:
01. Februar 2007 (online)

Abstract

Chiral vanadium complex prepared in situ from VO(acac)2 and Schiff base 9 was found to be an efficient catalyst for oxidation of various methyl aryl sulfides with hydrogen peroxide as terminal oxidant. For example, oxidation of methyl 2-naphthyl sulfide using a VO(acac)2, 9, and hydrogen peroxide system proceeded with high enantioselectivity of 93% ee as well as acceptable chemical yield.

13

Although we synthesized compound 8 according to the reported procedure (ref. [14] ), it can be prepared enantioselectively in a short step by using Yamamoto procedure (ref. [15] ).