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| Title
| - Facile Synthesis of Carbotetracycles via Gold(I)-Catalyzed Cyclization of Unactivated Cyclic 1-Aryl-6,8-dien-1-ynes
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| Abstract
| - The gold(I)-catalyzed cyclization of the cyclohexa-1,3-diene bearing a terminal alkyne and a gem-diester in the tether proceeds via a cationic gold intermediate to give a tetrahydromethyleneindene derivative. Changing the gem-diester to a gem-diketone in the tether, the transient gold-stabilized carbocation is trapped intramolecularly by a methyl ketone to afford a tricyclo[5.4.0.04,8]undecane ring skeleton. Under the same reaction conditions, aryl-substituted cyclohexadienynes afford hexahydroacephenanthrylene rings in a diastereoselective fashion and in good yields. The reaction proceeded via attack of the aryl group onto the gold-stabilized carbocations followed by aromatization and protodemetalation to generate the tetracarbocycles. This cycloaddition can be applied to the synthesis of pentahydronapthoazulenes from aryl-substituted cycloheptadienynes and the gold(I) catalyst.
- The gold(I) effectively catalyzed intramolecular cyclizations of aryl-substituted cyclohexadienynes to afford hexahydroacephenanthrylene rings in a diastereoselective fashion and in good yields, whereas pentahydronapthoazulenes can be obtained from aryl-substituted cycloheptadienynes and the gold(I) catalyst under the same reaction conditions.
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| - Facile Synthesis of Carbotetracycles
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