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Synthesis of Cyclic Alkenyl Ethers via Intramolecular Cyclization of O-Alkynylbenzaldehydes. Importance of Combination between CuI Catalyst and DMF
journal contribution
posted on 2004-07-23, 00:00 authored by Nitin T. Patil, Yoshinori YamamotoAn efficient and remarkably general method for
the synthesis of cyclic alkenyl ethers via the Cu(I)-catalyzed
intramolecular cyclization of O-alkynylbenzaldehydes has
been developed. The survey of metal catalysts and solvents
revealed that the combination of copper(I) iodide and DMF
was the catalytic system of choice. The reaction most probably proceeds via the nucleophilic addition of alcohols 2 to
O-alkynylbenzaldehydes 1 to generate the corresponding
hemiacetals, and subsequent nucleophilic attack of the
hemiacetal oxygen to the copper coordinated alkyne would
give the annulation products 3. In all cases, the reaction
proceeded in a regiospecific manner leading to the six-membered endocyclic products via 6-endo-dig cyclization.
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Keywords
regiospecific mannerCyclic Alkenyl EthersDMFnucleophilic additionintramolecularannulation products 3alkynylbenzaldehydes 1cyclic alkenyl ethersCombinationImportancenucleophilic attackcyclizationCuI CatalystsurveyiodidemethodsynthesissolventcombinationIntramolecular CyclizationAlkynylbenzaldehydechoicemetal catalystsproceedalcohols 2hemiacetal oxygenalkyneendocyclicendoSynthesi
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