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In our synthetic studies toward huperzine A, a diastereoselective α′-alkylation of the α-amido-γ-methyl hexenone 4 was realized through a dianion intermediate which significantly enhanced the reactivity. Under the attempted Heck reaction conditions, an unexpected and unprecedented palladium-catalyzed intramolecular γ-arylation of 3 was observed, which generated 18 with bicyclo[3.3.1]nonane framework in satisfactory yield.
In our synthetic studies toward huperzine A, a diastereoselective α’-alkylation of the α-amido-γ-methyl hexenone 4 was realized through a dianion intermediate which significantly enhanced the reactivity. Under the attempted Heck reaction conditions, an unexpected and withstanding palladium- catalyzed intramolecular γ-arylation of 3 was observed, which generated 18 with bicyclo [3.3.1] nonane framework in satisfactory yield.