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

doi:10.1016/j.tetasy.2006.01.016

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

Multidisciplinary chemistry

Research output: Contribution to journal › Article › peer-review

105 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 language	English
Pages (from-to)	521-535
Number of pages	15
Journal	Tetrahedron Asymmetry
Volume	17
Issue number	4
DOIs	https://doi.org/10.1016/j.tetasy.2006.01.016
Publication status	Published - Feb 20 2006

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/j.tetasy.2006.01.016

Cite this

@article{811fb0ec773f4be7861e3082938177ae,

title = "Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP",

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).",

author = "Ryoichi Kuwano and Manabu Kashiwabara and Koji Sato and Takashi Ito and Kohei Kaneda and Yoshihiko Ito",

note = "Funding Information: This work was supported by Kyushu University Foundation, the Naito Foundation, and Grant-in-Aids for Scientific Research on Priority Area 17035062 from MEXT. ",

year = "2006",

month = feb,

day = "20",

doi = "10.1016/j.tetasy.2006.01.016",

language = "English",

volume = "17",

pages = "521--535",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "4",

}

TY - JOUR

T1 - Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP

AU - Kuwano, Ryoichi

AU - Kashiwabara, Manabu

AU - Sato, Koji

AU - Ito, Takashi

AU - Kaneda, Kohei

AU - Ito, Yoshihiko

N1 - Funding Information: This work was supported by Kyushu University Foundation, the Naito Foundation, and Grant-in-Aids for Scientific Research on Priority Area 17035062 from MEXT.

PY - 2006/2/20

Y1 - 2006/2/20

N2 - 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).

AB - 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).

UR - http://www.scopus.com/inward/record.url?scp=33645913553&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33645913553&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2006.01.016

DO - 10.1016/j.tetasy.2006.01.016

M3 - Article

AN - SCOPUS:33645913553

SN - 0957-4166

VL - 17

SP - 521

EP - 535

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 4

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this