Abstract
The lipase-catalysed kinetic resolution of methyl esters of (±)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxylic acid, (±)-6-chloro-2,3-dihydro-4 H-1-benzopyran-2-carboxylic acid, and (±)-6-chloro-2,3-dihydro-4 H-1-benzopyran-3-carboxylic acid, rigid analogues of clofibrate, was effected with fair to moderate enantioselectivities ( E=1.0–4.8), enantiomeric excesses 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 corresponding racemic acid with (+)- and (−)-amphetamine from ethanol; the absolute configuration of the products were established by chemical correlation.
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