Platinum(II)-Catalyzed Reaction of γ,δ-Ynones with Alkenes for the Construction of 8-Oxabicyclo[3.2.1]octane Skeletons: Generation of Platinum-Containing Carbonyl Ylides from Acyclic Precursors


  • This research was partly supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. H.F. was granted a Research Fellowship of the Japan Society for the Promotion of Science for Young Scientists.


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Two types of bicycles can be prepared selectively by the title reaction, depending on whether or not a substituent is present at the propargylic position of the ynone substrate (see scheme). The cycloaddition of carbonyl ylides derived from γ,δ-ynones with vinyl ethers (or styrene) gave intermediate bicyclic carbene complexes, which underwent a 1,2-hydrogen-atom shift or rearrangement to provide the products. R1=alkyl, Ph; R3=alkyl.