Highly enantioselective phosphination and hydrophosphonylation of azomethine imines: using chiral squaramide as a hydrogen bonding organocatalyst

Org Biomol Chem. 2014 Nov 21;12(43):8656-70. doi: 10.1039/c4ob01472c.

Abstract

Enantioselective phosphination and hydrophosphonylation reactions between azomethine imines and diarylphosphine oxides or dialkyl phosphites were respectively developed by the use of a chiral squaramide as the hydrogen bonding organocatalyst, which afforded two types of phosphorus containing product in high yields with good to excellent enantioselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemistry*
  • Catalysis
  • Cyclobutanes / chemistry*
  • Hydrogen Bonding
  • Imines / chemistry*
  • Molecular Structure
  • Oxides
  • Phosphines / chemistry*
  • Stereoisomerism
  • Sulfonamides / chemistry*
  • Thiosemicarbazones / chemistry*

Substances

  • Azo Compounds
  • Cyclobutanes
  • Imines
  • Oxides
  • Phosphines
  • Sulfonamides
  • Thiosemicarbazones
  • squaric acid amide