Asymmetric borane reduction of prochiral ketone using chiral bis(alpha, alpha-diphenyl-2-pyrrolidinemethanol) carbonate

Chem Pharm Bull (Tokyo). 2003 Feb;51(2):221-3. doi: 10.1248/cpb.51.221.

Abstract

Chiral bis(alpha, alpha-diphenyl-2-pyrrolidinemethanol) carbonate (DPP(2).H(2)CO(3)) is a useful asymmetric auxiliary for the asymmetric borane reduction of prochiral ketones. Chiral DPP(2).H(2)CO(3) is recoverable from the reaction and directly reusable for the reaction. The intermediate of KUR-1246, which we are developing as a new uterine relaxant, was synthesized using the methodology.

MeSH terms

  • Boranes / chemistry*
  • Boranes / metabolism
  • Carbonates / chemistry
  • Carbonates / metabolism
  • Methanol / chemistry
  • Methanol / metabolism
  • Oxidation-Reduction
  • Pyrrolidines / chemistry*
  • Pyrrolidines / metabolism
  • Stereoisomerism

Substances

  • Boranes
  • Carbonates
  • Pyrrolidines
  • Methanol