(E)-5-(Tributylstannylmethylidene)-5H-furan-2-ones: versatile synthons for the stereospecific elaboration of gamma-alkylidenebutenolide skeletons.
[reaction: see text] Stereoselective construction of (E)-gamma-tributylstannylmethylidene butenolides 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 in the Stille reaction was found to be dependent on the nature of the aryl halide.
Rousset
S
S
Laboratoire de Physicochimie des Interfaces et des Milieux Réactionnels, Faculté des Sciences de Tours, Parc de Grandmont, 37200 Tours, France.
Abarbri
M
M
Thibonnet
J
J
Duchêne
A
A
Parrain
J L
JL
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002384:Catalysis; D002852:Chromatography, Ion Exchange; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium; D012997:Solvents; D013237:Stereoisomerism; D013816:Thermodynamics; D014220:Trialkyltin Compounds / Q000138:chemical synthesis*
D005663:Furans; D007202:Indicators and Reagents; D012997:Solvents; D014220:Trialkyltin Compounds; D010165:Palladium; C004511:butenolide; D015107:4-Butyrolactone