Asymmetric β-boration of α,β-unsaturated N-acyloxazolidinones by [2.2]paracyclophane-based bifunctional catalyst

Org Lett. 2012 Nov 16;14(22):5780-3. doi: 10.1021/ol302839d. Epub 2012 Nov 6.

Abstract

An efficient copper-catalyzed asymmetric conjugate boration has been achieved by exploiting a new planar and central chiral bicyclic triazolium ligand. This protocol was highly efficient and gave a variety of chiral secondary alkylboronates in 97-99% ee. A preliminary mechanistic study supports the bifunctional nature of the catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry
  • Catalysis
  • Copper / chemistry*
  • Esters
  • Molecular Structure
  • Oxazoles / chemical synthesis
  • Oxazoles / chemistry*
  • Stereoisomerism
  • Triazoles / chemical synthesis
  • Triazoles / chemistry

Substances

  • Boron Compounds
  • Esters
  • Oxazoles
  • Triazoles
  • Copper