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


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2004-03

AUTHORS

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

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. More... »

PAGES

693-702

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/b:rucb.0000035659.02761.1a

DOI

http://dx.doi.org/10.1023/b:rucb.0000035659.02761.1a

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1030741915


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