2016•The Journal of Organic ChemistryOpen access

Synthesis of a 1,3-Bridged Macrobicyclic Enyne via Chemoselective Cycloisomerization Using Palladium-Catalyzed Alkyne–Alkyne Coupling

Barry M. Trost, James T. Masters, Franck Le Vaillant, Jean‐Philip Lumb

Abstract

A unique intramolecular Pd-catalyzed alkyne-alkyne coupling is presented. This transformation generates a strained, 1,3-bridged, macrocyclic enyne. The process was readily executed on gram scale, and the structure of the product was elucidated via X-ray crystallographic analysis. A mechanistic rationale for the observed chemoselectivity is provided.

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Key concepts: Alkyne, Enyne, Chemoselectivity, Cycloisomerization, Chemistry, Intramolecular force, Catalysis, Palladium