Louisa Aribi‐Zouioueche, J. Fiaud
May 29, 2000
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0
Influential Citations
14
Citations
Journal
Tetrahedron Letters
Abstract
AbstractAcenaphthenyl acetate and acenaphthenol are resolved through Pseudomonas fluorescens lipase (PFL)-catalyzedhydrolysis and acylation, respectively. By contrast, the structurally related 1-(1-naphthyl)ethyl acetate and 1-(1-naphthyl)ethanol are inactive under the same reaction conditions. © 2000 Elsevier Science Ltd. All rights reserved. Keywords: kinetic resolution; enzyme; catalysis; enantioselective; acylation; hydrolysis. Enantiomerically pure 1-arylethanols and their derivatives are compounds of interest in transitionmetal-catalyzed organic synthesis. Noteworthy, 1-(1-naphthyl)ethyl acetate and carbonate have been usedas chiral, optically active substrates in palladium-catalyzed substitutions. 1 In this context, we have beeninterested in the preparation of optically active 1-acenaphthenol to investigate the behaviour of its estersin Pd-catalyzed substitutions. ( )-1-Acenaphthenol1, a benzylic alcohol which is an early metabolite ofoxidation of acenaphthene, has already been obtained by fractional crystallization of the diastereomericcamphanic esters and its configuration shown to be R by X-ray diffraction.