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Synthesis 1991; 1991(5): 342-346
DOI: 10.1055/s-1991-26460
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A Stereoselective Synthesis of 1-Substituted 2-Alkoxy-1,3-butadienes by the Fragmentation of ß-Hydroxysilanes

William H. Pearson* , Jeffrey M. Schkeryantz
  • *Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA
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Publikationsdatum:
29. April 2002 (online)

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Condensation of 3-(9-borabicyclo[3.3.1]nonan-9-yl)-1-[(diisopropylamino)carbonyloxy]-1-trimethylsilyl-1-propene with aldehydes followed by either acidic or basic workup afforded 1-substituted (Z)- or (E)-2-[(diisopropylamino)carbonyloxy]-1,3-butadienes, respectively, via fragmentation of an intermediate ß-hydroxysilane. A similar process gave an (E)-2-(methoxy)methoxy-1,3-butadiene.

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