doi:10.1016/j.tetlet.2003.10.208 
Copyright © 2003 Elsevier Ltd All rights reserved.
On the use of succinic anhydride as acylating agent for practical resolution of aryl–alkyl alcohols through lipase-catalyzed acylation
aGroupe de Synthèse Asymétrique et Biocatalyse, Université d’Annaba, 23000, Algeria
bLaboratoire de Catalyse moléculaire, Université de Paris-Sud, 91405 Orsay cedex, France
Received 27 August 2003;
accepted 17 October 2003.
Available online 2 December 2003.
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Abstract
A comparison is carried out of the E-values recorded in the lipase-catalyzed resolution of a series of secondary aryl–alkyl alcohols with enol esters versus succinic anhydride. Whereas all the substrates could be resolved by a proper choice of the lipase/enol ester couple with moderate (E=50) to good (E>100) enantioselectivities, only some of them showed satisfactory enantioselectivity (E>50) with the use of succinic acid as acylating agent. Notably, indanol and 1-quinolin-3-yl-ethanol were resolved in a practical way, with E>100 and E>80, respectively.
Keywords: Alkyl–aryl secondary alcohols; Acylation; Candida antarctica lipase B (CAL B); Pseudomonas fluorescens lipase (PFL); Succinic anhydride
Scheme 1. Lipase-catalyzed acylation with enol acetates.
Scheme 2. Lipase-catalyzed acylation with succinic anhydride.
Table 1.
CAL B-catalyzed acylation of alcohols 1–9 with enol esters
d Determined by HPLC with a Chiralcel
® OD-H capillary column, after acylation (Ac
2O, DMAP, NEt
3).
a 2mmol in 10mL diethyl ether; 22–24h reaction time, unless otherwise stated. CAL B (300mg).
b Determined from HPLC of the mixture on a Chiralcel
® OD-H capillary column.
e Calculated from
E=ln[(1−
c)(1−ee
s)]/ln[(1−
c)(1+ee
s)]
13.
c After silica gel chromatography, hexane/ethyl acetate 80:20 (except for
9 60:40).
f 14h reaction time.
Table 2.
PFL-catalyzed acylation of alcohols 1–9 with enol esters
a2 mmol in 10 mL diethyl ether; 22–24 h reaction time, unless otherwise stated; PFL (50 mg).
b,c,d,eSee footnotes, Table 1.
f48 h reaction time.
g72 h reaction time.
Table 3.
CAL B-catalyzed acylation of alcohols 1–9 with succinic anhydride
a,b,c,d,eSee footnotes, Table 1.
f14 h reaction time.
Table 4.
PFL-catalyzed acylation of alcohols 1–8 with succinic anhydride
a,b,c,d,eSee footnotes, Table 1.
f48 h reaction time.
g96 h reaction time.
h72 h reaction time.
Abstract
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