A novel synthesis of optically active C2-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents

Hiyoshizo Kotsuki; Yuichi Nakagawa; Narimasa Moriya; Hirotaka Tateishi; Masamitsu Ochi; Takayoshi Suzuki; Kiyoshi Isobe

doi:10.1016/0957-4166(95)00142-C

A novel synthesis of optically active C₂-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents

Hiyoshizo Kotsuki, Yuichi Nakagawa, Narimasa Moriya, Hirotaka Tateishi, Masamitsu Ochi, Takayoshi Suzuki, Kiyoshi Isobe

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

23 Citations (Scopus)

Abstract

A variety of optically active C₂-symmetric pyridine derivatives have been prepared from L- or D-tartaric acid as a chiral source via efficient coupling reactions of triflates with 2-picolyllithium reagents, and the utility of 17 and 18 as chiral ligands in the catalytic enantioselective addition of diethylzinc to benzaldehyde has been demonstrated (up to 41% ee). The synthetic procedure for the corresponding meso-isomer was also described.

Original language	English
Pages (from-to)	1165-1174
Number of pages	10
Journal	Tetrahedron: Asymmetry
Volume	6
Issue number	5
DOIs	https://doi.org/10.1016/0957-4166(95)00142-C
Publication status	Published - May 1995
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/0957-4166(95)00142-C

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title = "A novel synthesis of optically active C2-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents",

abstract = "A variety of optically active C2-symmetric pyridine derivatives have been prepared from L- or D-tartaric acid as a chiral source via efficient coupling reactions of triflates with 2-picolyllithium reagents, and the utility of 17 and 18 as chiral ligands in the catalytic enantioselective addition of diethylzinc to benzaldehyde has been demonstrated (up to 41% ee). The synthetic procedure for the corresponding meso-isomer was also described.",

author = "Hiyoshizo Kotsuki and Yuichi Nakagawa and Narimasa Moriya and Hirotaka Tateishi and Masamitsu Ochi and Takayoshi Suzuki and Kiyoshi Isobe",

year = "1995",

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doi = "10.1016/0957-4166(95)00142-C",

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T1 - A novel synthesis of optically active C2-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents

AU - Kotsuki, Hiyoshizo

AU - Nakagawa, Yuichi

AU - Moriya, Narimasa

AU - Tateishi, Hirotaka

AU - Ochi, Masamitsu

AU - Suzuki, Takayoshi

AU - Isobe, Kiyoshi

PY - 1995/5

Y1 - 1995/5

N2 - A variety of optically active C2-symmetric pyridine derivatives have been prepared from L- or D-tartaric acid as a chiral source via efficient coupling reactions of triflates with 2-picolyllithium reagents, and the utility of 17 and 18 as chiral ligands in the catalytic enantioselective addition of diethylzinc to benzaldehyde has been demonstrated (up to 41% ee). The synthetic procedure for the corresponding meso-isomer was also described.

AB - A variety of optically active C2-symmetric pyridine derivatives have been prepared from L- or D-tartaric acid as a chiral source via efficient coupling reactions of triflates with 2-picolyllithium reagents, and the utility of 17 and 18 as chiral ligands in the catalytic enantioselective addition of diethylzinc to benzaldehyde has been demonstrated (up to 41% ee). The synthetic procedure for the corresponding meso-isomer was also described.

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U2 - 10.1016/0957-4166(95)00142-C

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VL - 6

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EP - 1174

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 5

ER -

A novel synthesis of optically active C₂-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents

Abstract

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