Manganese-Catalyzed Oxidative Transformation of Silyl Ethers to Ketones: Enantioselective Synthesis of Optically Active β- and γ-Siloxyketones

Shun-Ichi Murahashi; Satoru Noji; Tatsuo Hirabayashi; Naruyoshi Komiya

doi:10.1055/s-2004-829577

LETTER

Manganese-Catalyzed Oxidative Transformation of Silyl Ethers to Ketones: Enantioselective Synthesis of Optically Active β- and γ-Siloxyketones

Shun-Ichi Murahashi*^a,b, Satoru Noji^b, Tatsuo Hirabayashi^b, Naruyoshi Komiya^b
^a Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, 1-1, Ridai-cho, Okayama, Okayama 700-0005, Japan
Fax: +81(86)2564292; e-Mail: murahashi@high.ous.ac.jp;
^b Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1-3, Machikaneyama, Toyonaka, Osaka 560-8531, Japan

Abstract

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Abstract

(Salen)manganese(III)-catalyzed oxidation of silyl ethers with iodosylbenzene gave the corresponding carbonyl compounds. The enantioselective oxidation of symmetrical 1,3- and 1,4-disilyl ethers gave the corresponding optically active b- and g-siloxyketones, respectively (up to 93% ee).

Key words

asymmetric oxidation - silyl ethers - manganese catalyst - iodosylbenzene - siloxyketones

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References

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