Preparation of Dienylstannanes Via Pd Catalyzed Regio- and Stereocontrolled Addition Reactions
- 1 January 1994
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1994 (12) , 1267-1271
- https://doi.org/10.1055/s-1994-25678
Abstract
Using palladium-catalyzed addition reactions, a terminal alkyne, an alkynoate, and a tin hydride comprise the building blocks for the construction of 4-stannyl-(E,E)-2,4-dienoates in an atom-economical fashion. A terminal alkyne undergoes clean cis-1,2-addition to an internal alkynoate in the presence of catalytic palladium(II) acetate and tris(2,6-dimethoxyphenyl)phosphine to produce a 2-en-4-ynoate. Anti-Markovnikov cis-addition of tin hydride to the acetylenic function of the 2-en-4-ynoate occurs in the presence of in situ generated tetrakis(triphenylphosphine)palladium.Keywords
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