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Issue 24, 2000
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Synthesis and reactions of Biginelli-compounds. Part 23. Chemoenzymatic syntheses of enantiomerically pure 4-aryl-3,4-dihydropyrimidin-2(1H )-ones

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Abstract

Enantiomerically pure dihydropyrimidones (DHPMs) were prepared by lipase-catalyzed enzymatic resolution of two types of activated DHPM esters. In the first model series, pivaloyloxymethyl-activated DHPM C5-esters 10a–c were resolved on an analytical scale by various lipases in two different solvent systems with selectivities E < 50. Alternatively, attachment of an acetoxymethyl residue at the N3 position of the DHPM scaffold led to activated ester 15, which was selectively cleaved by Thermomyces lanuginosus lipase (E > 200) to furnish, after deprotection, DHPMs (R)- and (S )-13 on a semi-preparative scale. Treatment of (R)-13 with trichloroacetyl isocyanate produced the antihypertensive agent (R)-SQ 32926.

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Publication details

The article was received on 03 Aug 2000, accepted on 01 Nov 2000 and first published on 30 Nov 2000


Article type: Paper
DOI: 10.1039/B006372J
Citation: J. Chem. Soc., Perkin Trans. 1, 2000,0, 4382-4389
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    Synthesis and reactions of Biginelli-compounds. Part 23. Chemoenzymatic syntheses of enantiomerically pure 4-aryl-3,4-dihydropyrimidin-2(1H )-ones

    B. Schnell, W. Krenn, K. Faber and C. O. Kappe, J. Chem. Soc., Perkin Trans. 1, 2000, 0, 4382
    DOI: 10.1039/B006372J

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