S. Rousset et al., (E)-5-(tributylstannylmethylidene)-5H-furan-2-ones: Versatile synthons forthe stereospecific elaboration of gamma-alkylidenebutenolide skeletons, ORG LETT, 1(5), 1999, pp. 701-703
[GRAPHICS]
Stereoselective construction of (E)-gamma-tributylstannylmethylidene buteno
lides 1 was achieved through the palladium-catalyzed tandem cross coupling/
cyclization reactions of tributylstannyl 3-iodopropenoate derivatives with
tributyltinacetylene. Iododestannylation of 1 occurs with inversion of the
configuration of the exocyclic double bond while the observed selectivity i
n the Stille reaction was found to be dependent on the nature of the aryl h
alide.