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

22 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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A novel synthesis of optically active C₂-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents. / Kotsuki, Hiyoshizo; Nakagawa, Yuichi; Moriya, Narimasa; Tateishi, Hirotaka; Ochi, Masamitsu; Suzuki, Takayoshi; Isobe, Kiyoshi.

In: Tetrahedron: Asymmetry, Vol. 6, No. 5, 05.1995, p. 1165-1174.

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

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AU - Moriya, Narimasa

AU - Tateishi, Hirotaka

AU - Ochi, Masamitsu

AU - Suzuki, Takayoshi

AU - Isobe, Kiyoshi

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

Abstract

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