Stereoselective synthesis of disubstituted 3(2H)-furanones via catalytic intramolecular C-H insertion reactions of α-diazo-β-keto esters including asymmetric induction

Article abstract of DOI:10.1016/0040-4039(94)85379-7

Rhodium(II) catalysed decomposition of γ-alkoxy-α-diazo-β-ketoesters produce cis-2,5-disubstituted-3(2H) furanones with high (> 97%) stereoselectivity. The combination of a chiral auxiliary in the ester moiety of the diazo precursor and a chiral catalyst can lead to asymmetric synthesis with diastereoselectivities up to 61% de.