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Synthesis 1994; 1994(12): 1267-1271
DOI: 10.1055/s-1994-25678
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Preparation of Dienylstannanes Via Pd Catalyzed Regio- and Stereocontrolled Addition Reactions

Barry M. Trost* , Chao-Jun Li
  • *Department of Chemistry, Stanford University, California 94305-5080, USA
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Publication Date:
25 April 2002 (online)

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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.

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