Stille reactions of 2,3-bis(stannyl)butenoates: an unexpected regioselectivity

Carter, N.B., Mabon, R. and Sweeney, J.B. (2006) Stille reactions of 2,3-bis(stannyl)butenoates: an unexpected regioselectivity. Synlett, 2006 (10). pp. 1577-1579. ISSN 0936-5214 doi: 10.1055/s-2006-944207

Abstract/Summary

The palladium-catalyzed cross-coupling reaction of methyl (Z)-2,3-bis(tributylstannyl)butenoate with aryl iodides is regioselective, leading to 2-aryl-3-stannylated products; this selectivity is the opposite to that observed in the reaction between halides and 3,4-bis(stannyl)furan-2(5H)-one. Since the resulting butenoates can be converted into the corresponding furanones, the method provides useful flexibility in the preparation of functionalized butenoates and furanones.