The Reactivity of the Highly Functionalized Copper, Zinc Reagents RCu(CN)ZnI Toward 1-Haloalkynes and Acetylenic Esters
The highly functionalized organometallics RCu(CN)ZnI 1 react efficiently with 1-haloalkynes providing polyfunctionalized alkynes in high yields.This method has been used to prepare a pheromone of the Amathes c-nigrum in 3 steps and 64percent overall yield.The reagents 1 also add in the presence of an excess of Me3SiCl to acetylenic esters to afford polyfunctionalized C-silylated ethylenic esters.In the case of ethyl propiolate, the reaction is highly stereoselective and affords 97percent pure (E)-2-trimethylsilyl ethylenic esters.
Yeh, Ming Chang P.,Knochel, Paul
p. 4799 - 4802
(2007/10/02)
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