Login / Signup

Thiourea-catalysed conjugate additions of amines to vinyl phosphonates and phosphinates.

Peter E McDermottMartin P Ó FearraighAlexandra M HoranEoghan M McGarrigle
Published in: Organic & biomolecular chemistry (2023)
Thiourea catalysts activated α,β-unsaturated phosphonates and phosphinates toward conjugate addition by amines to give β-aminophosphonates and β-aminophosphinates. The organocatalytic methodology was used to synthesise 15 β-aminophosphonates and -phosphinates in yields up to 99%. A gram-scale example furnished the corresponding β-aminophosphonate in an isolated yield of 99% with 97% catalyst recovery. Based on mechanistic experiments, hydrogen bonding between the phosphoryl oxygen and thiourea are proposed to play a crucial role in substrate activation.
Keyphrases
  • highly efficient
  • cancer therapy
  • metal organic framework
  • gram negative
  • ionic liquid
  • room temperature
  • reduced graphene oxide
  • carbon dioxide
  • multidrug resistant
  • amino acid