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ChemInform Abstract: Addition of Z-Vinylic Higher Order Cyanocuprates to Hindered Enones. The Influence of the Reaction Conditions.

✍ Scribed by M. A. Araujo; R. E. Barrientos-Astigarraga; R. M. Ellensohn; J. V. Comasseto

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199938051

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Addition of Z-vinylic higher order cyano

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Z-Vinylic higher order cyanocuprates, prepared from the corresponding Z-vinylic tellurides, react efficiently with hindered enones in THF/BF3-Et20 or in diethyl ether. In neat THF the hindered enones fail to react with Z-vinyl cyanocuprates prepared in this way.

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AbstractÐTransmetalation reaction between Z-vinylic tellurides and higher order cyanocuprates generated the corresponding Z-vinylic cyanocuprates. Conjugate addition of these cuprates to enones followed by O-functionalization led to silyl enol ethers, vinyl phosphates and vinyl tri¯ates. The vinyl t

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Dilithium cyanocuprates R\*LCu(CN)Li2 (L=2-Th, Me) react with vinylic tellurides of Z configuration, RCH=CHTeRl to give higher order vinylic cyanocuprates, [(RCH=CH)LCu(CN)Li2]. By changing the gegenion from lithium to magnesium [R2LCu(CN)LiMgBr or R2LCu(CN)(MgBr)2] the reaction gives cross -couplin

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