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 - May 1995
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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