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Synlett 2009(7): 1095-1098  
DOI: 10.1055/s-0028-1088156
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

An Effective Catalytic Epoxidation of Terpenes with Hydrogen Peroxide ­under Organic Solvent-Free Conditions

Yoshihiro Kon, Yutaka Ono, Tomohiro Matsumoto, Kazuhiko Sato*
National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5 Higashi 1-1-1, Tsukuba, Ibaraki 305-8565, Japan
Fax: +81(29)8614578; e-Mail: k.sato@aist.go.jp;
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Publication History

Received 26 December 2008
Publication Date:
20 March 2009 (online)

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Abstract

A catalytic system that operates well for the epoxidation of α-pinene, a very challenging substrate, at near-neutral pH and ambient temperature without organic solvent was developed. With hydrogen peroxide as a terminal oxidant, combination of Na2WO4, PhP(O)(OH)2, and [Me(n-C8H17)3N]HSO4 successfully catalyzed the epoxidation of α-pinene to give α-pinene oxide in 95% selectivity at 91% conversion, while the previously published conditions that use NH2CH2P(O)(OH)2 as a promoter provide no epoxide. The method is also well applicable to the epoxidation of the other acid-sensitive terpenes.

Key words

oxidations - catalysis - epoxides - terpenoids - green chemistry

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