15088-38-7Relevant academic research and scientific papers
Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives
Miura, Masahiro,Enna, Masahiro,Okuro, Kazumi,Nomura, Masakatsu
, p. 4999 - 5004 (1995)
Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza-1-buten-3-ynes in good yields.In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products.The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used.Asymmetric induction is also observed in the reaction of phenylacetylene with α,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.
NOVEL MECHANISTIC ASPECTS OF THE 4-ACYL-β-LACTAM FORMATION FROM 1,2-IMINOKETONES
Alcaide, Benito,Dominguez, Gema,Plumet, Joaquin,Sierra, Miguel A.
, p. 1317 - 1320 (2007/10/02)
On the basis of chemical and stereochemical evidence the course of the formation of 4-acyl-β-lactams from 1,2-iminoketones by reaction with the acyl chloride/Et3N system or with the preformed ketene is discussed.
