A stereoselective synthesis of 1-substituted 2-alkoxy-1,3-butadienes by the fragmentation of β-hydroxysilanes

Article abstract of DOI:10.1055/s-1991-26460

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 β-hydroxysilane. A similar process gave an (E)-2-(methoxy)methoxy-1,3-butadiene.