A trans-chelating bisphosphine possessing only planar chirality and its application to catalytic asymmetric reactions

Ryoichi Kuwano, Takashi Uemura, Makoto Saitoh, Yoshihiko Ito

研究成果: ジャーナルへの寄稿記事

40 引用 (Scopus)

抄録

A new chiral bisphosphine, (S,S)-2,2″-bis[(diethylphosphino)methyl]- 1,1″-biferrocene [(S,S)-EtTRAP-H], was synthesized in seven steps in 45% overall yield from ferrocenyloxazoline derived from (S)-valinol. The new chiral phosphine has only planar chirality, and is able to form a trans-chelate metal complex. (S,S)-EtTRAP-H is an effective ligand in rhodium-catalyzed asymmetric hydrosilylation of ketones (up to 94% ee). In particular, the hydrosilylation of 2-octanone yielded (S)-2-octanol with 77% ee.

元の言語英語
ページ(範囲)2263-2271
ページ数9
ジャーナルTetrahedron Asymmetry
15
発行部数14
DOI
出版物ステータス出版済み - 7 26 2004

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Hydrosilylation
phosphine
Chirality
Chelation
rhodium
chirality
chelates
phosphines
ketones
Rhodium
ligands
Coordination Complexes
Metal complexes
Ketones
metals
Ligands
2-octanol
2-octanone
valinol

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

これを引用

A trans-chelating bisphosphine possessing only planar chirality and its application to catalytic asymmetric reactions. / Kuwano, Ryoichi; Uemura, Takashi; Saitoh, Makoto; Ito, Yoshihiko.

:: Tetrahedron Asymmetry, 巻 15, 番号 14, 26.07.2004, p. 2263-2271.

研究成果: ジャーナルへの寄稿記事

Kuwano, Ryoichi ; Uemura, Takashi ; Saitoh, Makoto ; Ito, Yoshihiko. / A trans-chelating bisphosphine possessing only planar chirality and its application to catalytic asymmetric reactions. :: Tetrahedron Asymmetry. 2004 ; 巻 15, 番号 14. pp. 2263-2271.
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abstract = "A new chiral bisphosphine, (S,S)-2,2″-bis[(diethylphosphino)methyl]- 1,1″-biferrocene [(S,S)-EtTRAP-H], was synthesized in seven steps in 45{\%} overall yield from ferrocenyloxazoline derived from (S)-valinol. The new chiral phosphine has only planar chirality, and is able to form a trans-chelate metal complex. (S,S)-EtTRAP-H is an effective ligand in rhodium-catalyzed asymmetric hydrosilylation of ketones (up to 94{\%} ee). In particular, the hydrosilylation of 2-octanone yielded (S)-2-octanol with 77{\%} ee.",
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AB - A new chiral bisphosphine, (S,S)-2,2″-bis[(diethylphosphino)methyl]- 1,1″-biferrocene [(S,S)-EtTRAP-H], was synthesized in seven steps in 45% overall yield from ferrocenyloxazoline derived from (S)-valinol. The new chiral phosphine has only planar chirality, and is able to form a trans-chelate metal complex. (S,S)-EtTRAP-H is an effective ligand in rhodium-catalyzed asymmetric hydrosilylation of ketones (up to 94% ee). In particular, the hydrosilylation of 2-octanone yielded (S)-2-octanol with 77% ee.

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