Tetrahedron Letters p. 2239 - 2242 (1988)
Update date:2022-07-30
Topics:
Andreini, Bianca Patrizia
Carpita, Adriano
Rossi, Renzo
In the stereospecific palladium-catalysed cross-coupling reaction of 1-alkynylzinc chlorides or (E)-1-alkenyl diisobutylalanes, (E)-2-bromovinyltrimethylsilane reacts preferentially, in the presence of the corresponding (Z)-stereoisomer to afford good yields of (E)-1-trimethylsilyl-1-en-3-ynes (4) or (1E,3E)-1-trimethylsilyl-1,3-dienes (6),respectively, having very high stereoisomeric purities.Compounds 4 are easily converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (5) by selective hydrometallation reactions, followed by protonolysis.
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