Ligand-controlled iron-catalyzed coupling of α-substituted β-ketoesters with phenols.
A chemo-, regio-, and stereoselective FeCl(3)/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.
Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 84105, Israel.
Regev
R
Parnes
Umesh A
UA
Kshirsagar
Aviya
A
Werbeloff
Clil
C
Regev
Doron
D
Pappo
D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010618:Phenanthrolines / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
D002712:Chlorides; D004952:Esters; D005290:Ferric Compounds; D007659:Ketones; D008024:Ligands; D010618:Phenanthrolines; D010636:Phenols; C024555:ferric chloride; C025205:1,10-phenanthroline