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Silver-Catalyzed 1,3-Acyloxy Migration/Diels–Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines

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posted on 2017-02-22, 00:00 authored by Yichao Zhao, Jianwen Jin, Joshua William Boyle, Bo Ra Lee, David Philip Day, Dewi Susanti, Guy James Clarkson, Philip Wai Hong Chan
A synthetic method to prepare partially hydrogenated isoquinolines efficiently from silver-mediated [3,3]-sigmatropic rearrangement/Diels–Alder reaction of 1,9-dien-4-yne esters is described. The reactions were shown to be robust with a wide variety of substitution patterns tolerated to provide the corresponding nitrogen-containing heterocyclic products in good to excellent yields. This includes examples containing a bridgehead sp3 quaternary carbon center as well as the cycloisomerization of one substrate to give the corresponding bicyclic adduct in excellent yield at the gram scale.

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