Structural requirements of a chiral ligand for the catalytic asymmetric addition of thiophenol to α,β-unsaturated esters

Kiyoshi Tomioka; Manabu Okuda; Katsumi Nishimura; Shino Manabe; Motomu Kanai; Yasuo Nagaoka; Kenji Koga

doi:10.1016/S0040-4039(98)00080-X

Structural requirements of a chiral ligand for the catalytic asymmetric addition of thiophenol to α,β-unsaturated esters

Kiyoshi Tomioka, Manabu Okuda, Katsumi Nishimura, Shino Manabe, Motomu Kanai, Yasuo Nagaoka, Kenji Koga

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

2 Citations (Scopus)

Abstract

The tridentate amino ether ligands 1 and 14 were developed through systematic structural modification of the bidentate diether ligand 2. The reaction of thiophenol with methyl crotonate was catalyzed by 14 and lithium thiophenolate to afford (S)-methyl 3-phenylthiobutanoate in 75% ee and 95% yield.

Original language	English
Pages (from-to)	2141-2144
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4039(98)00080-X
Publication status	Published - 1998 Apr 9
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(98)00080-X

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title = "Structural requirements of a chiral ligand for the catalytic asymmetric addition of thiophenol to α,β-unsaturated esters",

abstract = "The tridentate amino ether ligands 1 and 14 were developed through systematic structural modification of the bidentate diether ligand 2. The reaction of thiophenol with methyl crotonate was catalyzed by 14 and lithium thiophenolate to afford (S)-methyl 3-phenylthiobutanoate in 75% ee and 95% yield.",

author = "Kiyoshi Tomioka and Manabu Okuda and Katsumi Nishimura and Shino Manabe and Motomu Kanai and Yasuo Nagaoka and Kenji Koga",

note = "Funding Information: Acknowledgment: We gratefully acknowledge financial support from Japan Society for Promotion of Science (RFTF-96P00302), the Ministry of Education, Science, Sports and Culture, and the Science and Technology Agency, Japan.",

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T1 - Structural requirements of a chiral ligand for the catalytic asymmetric addition of thiophenol to α,β-unsaturated esters

AU - Tomioka, Kiyoshi

AU - Okuda, Manabu

AU - Nishimura, Katsumi

AU - Manabe, Shino

AU - Kanai, Motomu

AU - Nagaoka, Yasuo

AU - Koga, Kenji

N1 - Funding Information: Acknowledgment: We gratefully acknowledge financial support from Japan Society for Promotion of Science (RFTF-96P00302), the Ministry of Education, Science, Sports and Culture, and the Science and Technology Agency, Japan.

PY - 1998/4/9

Y1 - 1998/4/9

N2 - The tridentate amino ether ligands 1 and 14 were developed through systematic structural modification of the bidentate diether ligand 2. The reaction of thiophenol with methyl crotonate was catalyzed by 14 and lithium thiophenolate to afford (S)-methyl 3-phenylthiobutanoate in 75% ee and 95% yield.

AB - The tridentate amino ether ligands 1 and 14 were developed through systematic structural modification of the bidentate diether ligand 2. The reaction of thiophenol with methyl crotonate was catalyzed by 14 and lithium thiophenolate to afford (S)-methyl 3-phenylthiobutanoate in 75% ee and 95% yield.

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U2 - 10.1016/S0040-4039(98)00080-X

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M3 - Article

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SN - 0040-4039

VL - 39

SP - 2141

EP - 2144

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Structural requirements of a chiral ligand for the catalytic asymmetric addition of thiophenol to α,β-unsaturated esters

Abstract

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