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

Autor: Peter E. McDermott, Martin P. Ó. Fearraigh, Alexandra M. Horan, Eoghan M. McGarrigle
Rok vydání: 2023
Předmět:
Zdroj: Organicbiomolecular chemistry.
ISSN: 1477-0539
Popis: 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.
Databáze: OpenAIRE