Tetrahedron letters

Highly diastereoselective synthesis of (E)-1-trimethylsilyl-1-en-3-ynes,(1E, 3Z)-and (1E, 3E)-1-trimethylsilyl-1, 3-dienes

BP Andreini, A Carpita, R Rossi

Index: Andreini, Bianca Patrizia; Carpita, Adriano; Rossi, Renzo Tetrahedron Letters, 1988 , vol. 29, # 18 p. 2239 - 2242

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Citation Number: 20

Abstract

Abstract 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)- ...

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