Further utilization of mucohalic acids: palladium-free, regioselective etherification and amination of alpha,beta-dihalo gamma-methoxycarbonyloxy and gamma-acetoxy butenolides

Org Lett. 2003 Dec 25;5(26):5015-7. doi: 10.1021/ol035994n.

Abstract

Palladium-free etherification and amination of mucohalic acid methyl carbonates 1e (3,4-dichloro-5-methoxycarbonyloxy-5H-furan-2-one) and 1f (3,4-dibromo-5-methoxycarbonyloxy-5H-furan-2-one) and mucochloric acid acetate 1h (3,4-dichloro-5-acetoxy-5H-furan-2-one) was achieved to afford gamma-functionalized alpha,beta-unsaturated gamma-butyrolactones in good to excellent yield. [reaction: see text]