S. Ferorelli et al., Lipase-mediated kinetic resolution of rigid clofibrate analogues with lipid-modifying activity, TETRAHEDR-A, 12(6), 2001, pp. 853-862
The lipase-catalysed kinetic resolution of methyl (+/-)-6-chloro-2.3-dihydr
o-4H-1-benzopyran-2-carboxylic acid. and (+/-)-6-chloro-2,3-dihydro-4H-1-be
nzopyran-3-carboxylic acid, rigid analogues of clofibrate. was effected wit
h fair to moderate enantioselectivities (E = 1.0-4.8), enantiomeric excesse
s of up to 86%, and workable reaction rates. Enantiomerically pure (R)- and
( S)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acids were obtained by
fractional crystallisation of the diastereomeric salts of the correspondin
g racemic acid with (+)- and (-)-amphetamine from ethanol; the absolute con
figuration of the products were established by chemical correlation. (C) 20
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