Highly enantioselective titanium-catalyzed cyanation of imines at room temperature

Org Lett. 2010 Jan 15;12(2):264-7. doi: 10.1021/ol902540h.

Abstract

A highly active and enantioselective titanium-catalyzed cyanation of imines at room temperature is described. The catalyst used is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-beta-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields in 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.

MeSH terms

  • Catalysis
  • Imines / chemistry*
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Organometallic Compounds / chemistry*
  • Stereoisomerism
  • Temperature*
  • Titanium / chemistry*

Substances

  • Imines
  • Nitriles
  • Organometallic Compounds
  • Titanium