Catalytic Intramolecular Addition of Metal Carbenes to Remote Furans

Abstract

Diazo esters and diazo ketones linked to a furan undergo catalytic intramolecular addition of an intermediate metal carbene to the remote furan to form diendiones with ring sizes up to 17. Regioselectivity is catalyst dependent with addition to either the more or less substituted double bond. The high product yields and absence of need for high dilution suggest that this methodology is general for macrocycle preparations.