Recent Advances in Dynamic Kinetic Resolution by Chiral Bifunctional (Thio)urea- and Squaramide-Based Organocatalysts

Molecules. 2016 Oct 14;21(10):1327. doi: 10.3390/molecules21101327.

Abstract

The organocatalysis-based dynamic kinetic resolution (DKR) process has proved to be a powerful strategy for the construction of chiral compounds. In this feature review, we summarized recent progress on the DKR process, which was promoted by chiral bifunctional (thio)urea and squaramide catalysis via hydrogen-bonding interactions between substrates and catalysts. A wide range of asymmetric reactions involving DKR, such as asymmetric alcoholysis of azlactones, asymmetric Michael-Michael cascade reaction, and enantioselective selenocyclization, are reviewed and demonstrate the efficiency of this strategy. The (thio)urea and squaramide catalysts with dual activation would be efficient for more unmet challenges in dynamic kinetic resolution.

Keywords: (thio)urea; dynamic kinetic resolution; squaramide.

Publication types

  • Review

MeSH terms

  • Catalysis
  • Hydrogen Bonding
  • Kinetics
  • Molecular Structure
  • Quinine / analogs & derivatives*
  • Quinine / chemistry
  • Stereoisomerism
  • Thiourea / chemistry*

Substances

  • squaramide
  • Quinine
  • Thiourea