832711-97-4Relevant academic research and scientific papers
Lipase-mediated deracemization of secondary 1-phenyl-substituted propargylic alcohols of different topology
Vlasyuk,Gamalevich,Ignatenko,Serebryakov,Struchkova
, p. 693 - 702 (2004)
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.
The absolute configuration of (+)- And (-)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris
Vlasyuk,Voblikova,Gamalevich,Serebryakov
, p. 2032 - 2036 (2014/07/07)
Hydrogenation of the triple bond of (+)-1-phenylundec-4-yn-3-ol (obtained from (+)[η6 (3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH4-NiCl2?6H2O reagent system in MeOH leads to (-)1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives (R)-(-)acetoxydodecanoic acid, lactonization of which leads to the known (R)-(+)-4dodecanolide. The starting (+)-1phenylundec-4-yn-3-ol was thus shown to have the Sconfiguration.
