Diastereoselective Synthesis of Highly Functionalized Proline Derivatives

Molecules. 2022 Oct 14;27(20):6898. doi: 10.3390/molecules27206898.

Abstract

An efficient way to access highly functionalized proline derivatives was developed based on a Cu(I)-catalyzed reaction between CF3-substituted allenynes and tosylazide, which involved a cascade of [3 + 2]-cycloaddition/ketenimine and a rearrangement/Alder-ene cyclization to afford the new proline framework with a high diastereoselectivity.

Keywords: 1,2,3-triazoles; 1,6-allenynes; alder-ene reaction; catalysis; cycloaddition; prolines.

MeSH terms

  • Catalysis
  • Cyclization
  • Cycloaddition Reaction
  • Molecular Structure
  • Proline*
  • Stereoisomerism

Substances

  • Proline