(E)-5-(tributylstannylmethylidene)-5H-furan-2-ones: Versatile synthons forthe stereospecific elaboration of gamma-alkylidenebutenolide skeletons

Citation
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
Citations number
48
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
5
Year of publication
1999
Pages
701 - 703
Database
ISI
SICI code
1523-7060(19990909)1:5<701:(VSF>2.0.ZU;2-E
Abstract
[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.