132938-22-8Relevant academic research and scientific papers
Gold-catalyzed diastereoselective synthesis of α-fluoroenones from propargyl acetates
Hopkinson, Matthew N.,Giuffredi, Guy T.,Gee, Antony D.,Gouverneur, Véronique
supporting information; experimental part, p. 2737 - 2742 (2010/12/25)
A diastereoselective preparation of -fluoroenones from propargyl acetates has been developed proceeding via a gold-catalyzed rearrangement-fluorination cascade. Control reactions are consistent with a mechanism involving a gold-mediated 3,3-sigmatropic shift followed by a direct, nongold-catalyzed electrophilic fluorination of the allenyl acetate intermediate.
Lipase-mediated deracemization of secondary 1-phenyl-substituted propargylic alcohols of different topology
Vlasyuk,Gamalevich,Ignatenko,Serebryakov,Struchkova
, p. 693 - 702 (2007/10/03)
Acetylation of (±)-1-phenylnon-2-yn-1-ol, (±)-1-phenylhept-1- yn-3-ol, and (±)-1-phenylundec-4-yn-3-ol ((±)-5) in the presence of lipase from Candida cylindracea (CCL) proceeds slowly to give products with ee ≤20%. The acetates of these alcohols are hydrolyzed in the presence of porcine pancreatic lipase (PPL) equally unsatisfactorily. The (η6-arene)tricarbonylchromium complex of alcohol (±)-5 is acetylated in the presence of CCL up to ～22% conversion to give (R)-acetate whose oxidative decomplexation followed by saponification results in alcohol (R)-(-)-5 with ee ≥95%. The configuration of alcohols (-)-5 and (+)-5 was determined by NMR spectroscopy of their esters with (R)- and (S)-Mosher's acids.
On the palladium(II)-catalysed oxidative rearrangement of propargylic acetates
Bartels,Mahrwald,Mueller
, p. 483 - 485 (2007/10/03)
The catalytic transformation of propargylic acetates into the corresponding α-acetoxyenones in the presence of palladium(II) chloride is described. Water is a necessary component in this unusual oxidative rearrangement.
