Regioselective Alkynylation of Allylic Phosphates with Alkynyl Copper Reagents

We developed a regioselective alkynylation of allylic phosphates with alkynyl copper reagents. The reaction gave 1,4-enynes independent of steric hindrance or electronic effects of the substrate or nucleophile. Then, we efficiently synthesized intermediates in the synthesis of lipid metabolites using this reaction.

Abstract

We developed an alkynylation of allylic phosphates with acetylenes in the presence of copper and magnesium salts. The reaction proceeded regioselectively to afford the corresponding 1,4-enynes. Furthermore, the functional group tolerance of this reaction was established. As an application, the 1,4-enyne intermediate involved in the synthesis of 13R,19S,20S-trihydroxydocosapentaenoic acid could be efficiently synthesized.

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