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

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

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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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA 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(3):215-225.

Chicago/Turabian Style

Bouzemi, Nassima; Grib, Ismahane; Houiene, Zahia; Aribi-Zouioueche, Louisa. 2014. "Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount." Catalysts 4, no. 3: 215-225.


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