Synthesis 1994; 1994(12): 1267-1271
DOI: 10.1055/s-1994-25678
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
25 April 2002 (online)

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.