- Process for preparing 1,4 dihydropyridine compounds
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A 1,4-dihydropyridine derivative represented by formula (I): STR1 wherein X represents an alkyl group, or a group of STR2 in which R1, R2, and R3 may be the same or different and each represent a hydrogen atom, a halogen atom, a nitro group, a nitrile group, or a trifluoromethyl group; R4 represents a substituted or unsubstituted acyloxymethyl group, an alkoxycarbonyloxymethyl group, a (2-oxo-1,3-dioxolen-4 -yl)methyl group, a (5-substituted-2-oxo-1,3-dioxolen-4 -yl)methyl group, or an acyl group; R5 represents a lower alkyl group or a substituted alkyl group; and R6 represents a hydrogen atom, a lower alkoxymethyl group, or a lower acyloxymethyl group, is disclosed. The compound is stereospecifically hydrolyzed by the action of an enzyme to provide an optically active 1,4-dihydro -3-pyridinemonocarboxylic acid which is useful as an intermediate of pharmaceuticals in good optical purity and yield.
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- Acyloxymethyl as an activating group in lipase-catalyzed enantioselective hydrolysis. A versatile approach to chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates
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The first practical syntheses of chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates, which are attractive compounds as new calcium antagonists, were realized by lipase-catalyzed enantioselective hydrolysis of the acyloxymethyl esters. The monoesters obtained were revealed to have high optical purity and demonstrated to be useful chiral synthons.
- Ebiike,Terao,Achiwa
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p. 5805 - 5808
(2007/10/02)
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