Issue 13, 1995

Organolead-mediated arylation of allyl β-keto esters: selective synthesis of 2′-hydroxyisoflavones

Abstract

Arylation of the A-ring-unsubstituted and -substituted 3-(allyloxycarbonyl)chroman-4-ones 68 with [4,5-dimethoxy-2-(methoxymethoxy)phenyl]lead(IV) triacetate 5 followed by selective catalytic deallyloxycarbonylation–dehydrogenation afforded 2′-protected isoflavones in high overall yields. Acid-catalysed removal of the methoxymethyl group led to the corresponding 2′-hydroxyisoflavones.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1995, 1679-1683

Organolead-mediated arylation of allyl β-keto esters: selective synthesis of 2′-hydroxyisoflavones

D. M. X. Donnelly, J. Finet and B. A. Rattigan, J. Chem. Soc., Perkin Trans. 1, 1995, 1679 DOI: 10.1039/P19950001679

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