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Molecules 2012, 17(6), 6901-6915; doi:10.3390/molecules17066901

Catalytic Asymmetric Hydrogenation of 3-Substituted Benzisoxazoles

Department of Chemistry, Graduate School of Sciences, and International Research Center for Molecular Systems (IRCMS), Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
Author to whom correspondence should be addressed.
Received: 17 April 2012 / Revised: 2 June 2012 / Accepted: 4 June 2012 / Published: 6 June 2012
(This article belongs to the Special Issue Asymmetric Catalysis)
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A variety of 3-substituted benzisoxazoles were reduced with hydrogen using the chiral ruthenium catalyst, {RuCl(p-cymene)[(R,R)-(S,S)-PhTRAP]}Cl. The ruthenium-catalyzed hydrogenation proceeded in high yield in the presence of an acylating agent, affording a-substituted o-hydroxybenzylamines with up to 57% ee. In the catalytic transformation, the N–O bond of the benzisoxazole substrate is reductively cleaved by the ruthenium complex under the hydrogenation conditions. The C–N double bond of the resulting imine is saturated stereoselectively through the PhTRAP–ruthenium catalysis. The hydrogenation produces chiral primary amines, which may work as catalytic poisons, however, the amino group of the hydrogenation product is rapidly acylated when the reaction is conducted in the presence of an appropriate acylating agent, such as Boc2O or Cbz-OSu.
Keywords: ruthenium; catalytic asymmetric synthesis; hydrogenation; benzisoxazole; amine ruthenium; catalytic asymmetric synthesis; hydrogenation; benzisoxazole; amine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Ikeda, R.; Kuwano, R. Catalytic Asymmetric Hydrogenation of 3-Substituted Benzisoxazoles. Molecules 2012, 17, 6901-6915.

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