カルボカチオン活性種の設計を基盤とする炭素骨格構築法の開発

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  • Development of New Reactions for Carbon-Carbon Bond Formation by Using Carbocation Species.
  • カルボカチオン カッセイシュ ノ セッケイ オ キバン ト スル タンソ コッカク コウチクホウ ノ カイハツ

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New synthetic methods for functionalized carbocyclic compounds were developed on the basis of [3 + 2] and [5 + 2] cycloaddition reactions by using carbocation species. Under the influence of a Lewis acid, 3- (methylthio) -2-siloxyallyl acetates reacted with various kinds of olefins to afford the corresponding cyclopentanones in good yields. The sterically more hindered regioisomer was predominantly formed in every case, and surprisingly high stereoselectivity was also observed in certain cases. An efficient synthetic method for (-) -coriolin has been developed on the basis of the [3 + 2] cycloaddition reaction. On the other hand, 5-acetoxy-2- [(trimethylsilyl) methyl] -1-penten-3-yne-dicobalthexacarbonyl underwent [5 + 2] cycloaddition reactions with enol triisopropylsill ethers to give seven-membered compounds. The reactions with cyclic enol silyl ethers as well as acyclic enol silyl ethers exhibited remarkably high diastereoselectivity.

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