Chiral Bipyridine Ligand with Flexible Molecular Recognition Site: Development and Application to Copper-Catalyzed Asymmetric Borylation of α,β-Unsaturated Ketones

Ryosuke Tsutsumi, Rika Taguchi, Masahiro Yamanaka

Research output: Contribution to journalArticlepeer-review

Abstract

A novel chiral bipyridine ligand bearing a flexible side chain with a molecular recognition site enables precise stereocontrol through the cooperative action of metal center and hydrogen bonds. This new chiral ligand was applied to the copper-catalyzed asymmetric borylation of α,β-unsaturated carbonyl compounds. The reaction afforded the corresponding borylated products in good yields with high enantioselectivities. Preliminary studies of the functional group-selective transformation revealed that the newly designed chiral bipyridine ligand has the potential to control chemo- and site selectivity in addition to stereoselectivity.

Original languageEnglish
JournalChemCatChem
DOIs
Publication statusAccepted/In press - 2021
Externally publishedYes

Keywords

  • asymmetric catalysis
  • boron
  • copper
  • non-covalent interactions
  • β-borylation

ASJC Scopus subject areas

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

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