Tetrahedron Letters p. 4799 - 4802 (1989)
Update date:2022-08-06
Topics:
Yeh, Ming Chang P.
Knochel, Paul
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.
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