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Lipase-mediated deracemization of secondary 1-phenyl-substituted propargylic alcohols of different topology

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Russian Chemical Bulletin Aims and scope

Abstract

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.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. L. Vlasyuk, G. D. Gamalevich, A. V. Ignatenko, E. P. Serebryakov & M. I. Struchkova

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  1. A. L. Vlasyuk
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  2. G. D. Gamalevich
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  3. A. V. Ignatenko
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  4. E. P. Serebryakov
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  5. M. I. Struchkova
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Vlasyuk, A.L., Gamalevich, G.D., Ignatenko, A.V. et al. Lipase-mediated deracemization of secondary 1-phenyl-substituted propargylic alcohols of different topology. Russian Chemical Bulletin 53, 693–702 (2004). https://doi.org/10.1023/B:RUCB.0000035659.02761.1a

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