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 journalArticle

21 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 languageEnglish
Pages (from-to)1165-1174
Number of pages10
JournalTetrahedron Asymmetry
Volume6
Issue number5
DOIs
Publication statusPublished - 1995
Externally publishedYes

Fingerprint

Isomers
Pyridine
reagents
pyridines
isomers
Ligands
Derivatives
ligands
acids
Acids
synthesis
diethylzinc
tartaric acid
pyridine
benzaldehyde

ASJC Scopus subject areas

  • Catalysis
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

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, 1995, p. 1165-1174.

Research output: Contribution to journalArticle

Kotsuki, Hiyoshizo ; Nakagawa, Yuichi ; Moriya, Narimasa ; Tateishi, Hirotaka ; Ochi, Masamitsu ; Suzuki, Takayoshi ; Isobe, Kiyoshi. / A novel synthesis of optically active C2-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents. In: Tetrahedron Asymmetry. 1995 ; Vol. 6, No. 5. pp. 1165-1174.
@article{1bc5106152324ebea8488a7a17de9da0,
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",
doi = "10.1016/0957-4166(95)00142-C",
language = "English",
volume = "6",
pages = "1165--1174",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "5",

}

TY - JOUR

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

Y1 - 1995

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.

UR - http://www.scopus.com/inward/record.url?scp=0029059144&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029059144&partnerID=8YFLogxK

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

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

M3 - Article

AN - SCOPUS:0029059144

VL - 6

SP - 1165

EP - 1174

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 5

ER -