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Ligand-Controlled Iron-Catalyzed Coupling of α-Substituted β-Ketoesters with Phenols

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posted on 06.07.2012, 00:00 authored by Regev Parnes, Umesh A. Kshirsagar, Aviya Werbeloff, Clil Regev, Doron Pappo
A chemo-, regio-, and stereoselective FeCl3/1,10-phenanthroline-catalyzed cross dehydrogenative coupling (CDC) reaction between phenols and α-substituted β-ketoesters was developed. The reaction creates a new quaternary carbon center within a polycyclic hemiacetal or polycyclic spirolactone architecture. The applicability of the new method to the synthesis of natural products was demonstrated by a possible biomimetic synthesis of the lachnanthospirone core.