The reactivity of the highly functionalized copper, zinc reagents RCu(CN)ZnI toward 1-haloalkynes and acetylenic esters

Ming Chang P. Yeh, Paul Knochel

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Abstract

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 64% 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 97% pure (E)-2-trimethylsilyl ethylenic esters.

Original languageEnglish
Pages (from-to)4799-4802
Number of pages4
JournalTetrahedron Letters
Volume30
Issue number36
DOIs
Publication statusPublished - 1989

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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