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Silver-Catalyzed 1,3-Acyloxy Migration/Diels–Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines
journal contribution
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 ChanA 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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estersbridgehead sp 3 quaternary carbon centerEsterSilver-CatalyzedAcyloxysubstitution patterns-4-ynevarietysigmatropicDiencycloisomerizationPartially Hydrogenated Isoquinolinesmethodgram scalesilver-mediateddienbicyclic adducthydrogenated isoquinolinessubstrateyieldMigrationrearrangementnitrogen-containing heterocyclic products
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