Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles

Ryoichi Kuwano; Kohei Kaneda; Takashi Ito; Koji Sato; Takashi Kurokawa; Yoshihiko Ito

doi:10.1021/ol049317k

Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles

Ryoichi Kuwano, Kohei Kaneda, Takashi Ito, Koji Sato, Takashi Kurokawa, Yoshihiko Ito

Multidisciplinary chemistry

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

136 Citations (Scopus)

Abstract

N-Tosyl 3-substituted indoles were hydrogenated with high enantioselectivities (95-98% ee) by use of a trans-chelating chiral bisphosphine, (S,S)-(R,R)-PhTRAP ligand. The chiral catalyst, which was generated in situ from [Rh(nbd)₂]SbF6, PhTRAP, and Cs ₂CO₃, is useful for enantioselectively synthesizing a range of diverse optically active indolines possessing a chiral carbon at the 3-position.

Original language	English
Pages (from-to)	2213-2215
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	13
DOIs	https://doi.org/10.1021/ol049317k
Publication status	Published - Jun 24 2004

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol049317k

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abstract = "N-Tosyl 3-substituted indoles were hydrogenated with high enantioselectivities (95-98% ee) by use of a trans-chelating chiral bisphosphine, (S,S)-(R,R)-PhTRAP ligand. The chiral catalyst, which was generated in situ from [Rh(nbd)2]SbF6, PhTRAP, and Cs 2CO3, is useful for enantioselectively synthesizing a range of diverse optically active indolines possessing a chiral carbon at the 3-position.",

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

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T1 - Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles

AU - Kuwano, Ryoichi

AU - Kaneda, Kohei

AU - Ito, Takashi

AU - Sato, Koji

AU - Kurokawa, Takashi

AU - Ito, Yoshihiko

PY - 2004/6/24

Y1 - 2004/6/24

N2 - N-Tosyl 3-substituted indoles were hydrogenated with high enantioselectivities (95-98% ee) by use of a trans-chelating chiral bisphosphine, (S,S)-(R,R)-PhTRAP ligand. The chiral catalyst, which was generated in situ from [Rh(nbd)2]SbF6, PhTRAP, and Cs 2CO3, is useful for enantioselectively synthesizing a range of diverse optically active indolines possessing a chiral carbon at the 3-position.

AB - N-Tosyl 3-substituted indoles were hydrogenated with high enantioselectivities (95-98% ee) by use of a trans-chelating chiral bisphosphine, (S,S)-(R,R)-PhTRAP ligand. The chiral catalyst, which was generated in situ from [Rh(nbd)2]SbF6, PhTRAP, and Cs 2CO3, is useful for enantioselectively synthesizing a range of diverse optically active indolines possessing a chiral carbon at the 3-position.

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JO - Organic Letters

JF - Organic Letters

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Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles

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