Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP

Ryoichi Kuwano, Manabu Kashiwabara, Koji Sato, Takashi Ito, Kohei Kaneda, Yoshihiko Ito

Research output: Contribution to journalArticle

97 Citations (Scopus)

Abstract

Highly enantioselective hydrogenation of N-protected indoles was successfully developed by use of the rhodium catalyst generated in situ from [Rh(nbd)2]SbF6 and the chiral bisphosphine PhTRAP, which can form a trans-chelate complex with a transition metal atom. The PhTRAP-rhodium catalyst required a base (e.g., Cs2CO3) for the achievement of high enantioselectivity. Various 2-substituted N-acetylindoles were converted into the corresponding chiral indolines with up to 95% ee. The hydrogenations of 3-substituted N-tosylindoles yielded indolines possessing a stereogenic center at the 3-position with high enantiomeric excesses (up to 98% ee).

Original languageEnglish
Pages (from-to)521-535
Number of pages15
JournalTetrahedron Asymmetry
Volume17
Issue number4
DOIs
Publication statusPublished - Feb 20 2006

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Indoles
Rhodium
indoles
rhodium
Hydrogenation
hydrogenation
Ligands
catalysts
ligands
Catalysts
Enantioselectivity
chelates
Transition metals
transition metals
Atoms
atoms
indoline
N-tosylindole

All Science Journal Classification (ASJC) codes

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

Cite this

Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP. / Kuwano, Ryoichi; Kashiwabara, Manabu; Sato, Koji; Ito, Takashi; Kaneda, Kohei; Ito, Yoshihiko.

In: Tetrahedron Asymmetry, Vol. 17, No. 4, 20.02.2006, p. 521-535.

Research output: Contribution to journalArticle

Kuwano, Ryoichi ; Kashiwabara, Manabu ; Sato, Koji ; Ito, Takashi ; Kaneda, Kohei ; Ito, Yoshihiko. / Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP. In: Tetrahedron Asymmetry. 2006 ; Vol. 17, No. 4. pp. 521-535.
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