Ruthenium-catalyzed asymmetric hydrogenation of N-Boc-indoles

Ryoichi Kuwano; Manabu Kashiwabara

doi:10.1021/ol061039x

Ruthenium-catalyzed asymmetric hydrogenation of N-Boc-indoles

Ryoichi Kuwano, Manabu Kashiwabara

Multidisciplinary chemistry

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

165 Citations (Scopus)

Abstract

Highly enantioselective hydrogenation of various N-Boc-indoles proceeded successfully in the presence of the ruthenium complex generated from an appropriate ruthenium precursor and a trans-chelate chiral bisphosphine PhTRAP. Various 2- or 3-substituted indoles were converted into chiral indolines with high enantiomeric excesses (up to 95% ee). The PhTRAP-ruthenium catalyst was able to promote the hydrogenation of 2,3-dimethylindoles, giving cis-2,3-dimethylindolines with 72% ee.

Original language	English
Pages (from-to)	2653-2655
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	12
DOIs	https://doi.org/10.1021/ol061039x
Publication status	Published - Jun 8 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol061039x

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abstract = "Highly enantioselective hydrogenation of various N-Boc-indoles proceeded successfully in the presence of the ruthenium complex generated from an appropriate ruthenium precursor and a trans-chelate chiral bisphosphine PhTRAP. Various 2- or 3-substituted indoles were converted into chiral indolines with high enantiomeric excesses (up to 95% ee). The PhTRAP-ruthenium catalyst was able to promote the hydrogenation of 2,3-dimethylindoles, giving cis-2,3-dimethylindolines with 72% ee.",

author = "Ryoichi Kuwano and Manabu Kashiwabara",

year = "2006",

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doi = "10.1021/ol061039x",

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N2 - Highly enantioselective hydrogenation of various N-Boc-indoles proceeded successfully in the presence of the ruthenium complex generated from an appropriate ruthenium precursor and a trans-chelate chiral bisphosphine PhTRAP. Various 2- or 3-substituted indoles were converted into chiral indolines with high enantiomeric excesses (up to 95% ee). The PhTRAP-ruthenium catalyst was able to promote the hydrogenation of 2,3-dimethylindoles, giving cis-2,3-dimethylindolines with 72% ee.

AB - Highly enantioselective hydrogenation of various N-Boc-indoles proceeded successfully in the presence of the ruthenium complex generated from an appropriate ruthenium precursor and a trans-chelate chiral bisphosphine PhTRAP. Various 2- or 3-substituted indoles were converted into chiral indolines with high enantiomeric excesses (up to 95% ee). The PhTRAP-ruthenium catalyst was able to promote the hydrogenation of 2,3-dimethylindoles, giving cis-2,3-dimethylindolines with 72% ee.

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JO - Organic Letters

JF - Organic Letters

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Ruthenium-catalyzed asymmetric hydrogenation of N-Boc-indoles

Abstract

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