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Catalysts 2014, 4(3), 215-225; doi:10.3390/catal4030215

Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount

Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Department of Chemistry, Badji Mokhtar Annaba-University, B.P. 12, 23000 Annaba, Algeria
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Received: 13 February 2014 / Revised: 4 April 2014 / Accepted: 23 May 2014 / Published: 26 June 2014
(This article belongs to the Special Issue Enzymes in Organic Synthesis)
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Abstract

A series of arylalkylcarbinol derivatives were deracemized through sequential combination of Candida antarctica lipase B (CAL-B) catalyzed resolution by hydrolysis and Mitsunobu stereoinversion. The (S)-acetates were obtained in 71%–99% ee and 76%–89% yields. An enantiocomplementarity was established for the hydrolysis and acylation reactions with CAL-B lipase. Thus, the (S) and (R) enantiomers of Indan-1-yl acetate, 1,2,3,4-tetrahydro-1-naphthalenol acetate and 1-(2-naphthyl) ethyl acetate were obtained in 91%–99% ee and 76%–89% yield.
Keywords: deracemisation; lipase; hydrolysis; stereoinversion; arylalkylcarbinol deracemisation; lipase; hydrolysis; stereoinversion; arylalkylcarbinol
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Bouzemi, N.; Grib, I.; Houiene, Z.; Aribi-Zouioueche, L. Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount. Catalysts 2014, 4, 215-225.

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