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Communication | Special issue | Vol 76, No. 1, 2008, pp.191-196
Published online, 21st April, 2008
DOI: 10.3987/COM-08-S(N)37
Asymmetric Oxidation of Cyclic Sulfides Catalyzed by an Aluminum(salalen) Complex as the Catalyst

Kazuhiro Matsumoto, Tetsufumi Yamaguchi, and Tsutomu Katsuki*

*Department of Chemistry, Faculty of Science, Graduate School, Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

Abstract

We report a catalytic asymmetric oxidation of cyclic sulfides that uses a combination of aluminum(salalen) complex 1 as the catalyst and aqueous hydrogen peroxide as the oxidant. Oxidations of six-membered cyclic sulfides, thiochroman-4-ones, furnish the corresponding sulfoxides in high yield with high enantioselectivity. Five-membered 2,3-dihydrobenzo[b]thiophene and seven-membered dibenzo[b,e]thiepin-11(6H)-one are also good substrates for the aluminum-catalyzed system.