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Addition of Z-vinylic higher order cyanocuprates to hindered enones. The influence of the reaction conditions

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

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
175 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

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