Catalytic asymmetric hydrogenation of 3-substituted benzisoxazoles

Ryuhei Ikeda, Ryoichi Kuwano

研究成果: ジャーナルへの寄稿記事

12 引用 (Scopus)

抄録

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 α-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 Boc 2O or Cbz-OSu.

元の言語英語
ページ(範囲)6901-6915
ページ数15
ジャーナルMolecules
17
発行部数6
DOI
出版物ステータス出版済み - 6 1 2012

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Hydrogenation
Ruthenium
ruthenium
hydrogenation
poisons
Imines
Poisons
Catalysis
imines
catalysis
Amines
Hydrogen
amines
catalysts
Catalysts
Substrates
hydrogen
products

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

これを引用

Catalytic asymmetric hydrogenation of 3-substituted benzisoxazoles. / Ikeda, Ryuhei; Kuwano, Ryoichi.

:: Molecules, 巻 17, 番号 6, 01.06.2012, p. 6901-6915.

研究成果: ジャーナルへの寄稿記事

Ikeda, Ryuhei ; Kuwano, Ryoichi. / Catalytic asymmetric hydrogenation of 3-substituted benzisoxazoles. :: Molecules. 2012 ; 巻 17, 番号 6. pp. 6901-6915.
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