Nickel(0) catalyzed (2+2) cross-addition of bicyclo(2.2.1)heptene derivatives with electron-deficient olefins.

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概要

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• In the presence of bis(acrylonitrile)nickel(0) or bis(1,5-cyclooctadiene)nickel(0), <I>exo</I>-tricyclo[3.2.1.0<SUP>2,4</SUP>]oct-6-ene cycloadds to acrylonitrile and methyl acrylate to give <I>anti</I>- and <I>syn</I>-3-cyano-<I>exo</I>,<I>exo</I>-tetracyclo[4.3.1.0<SUP>2,5</SUP>.0<SUP>7,9</SUP>]decane or the corresponding methoxycarbonyl derivatives. The cycloaddition with dimethyl maleate proceeds with retention of configuration. Benzonorbornadiene also enters into the 2+2 reaction, while <I>endo</I>-tricyclo[3.2.1.0<SUP>2,4</SUP>]oct-6-ene, bicyclo[2.2.1]heptene, and 5-methylenebicyclo[2.2.1]heptene are unreactive. Origins of the observed selectivities in the catalyzed reaction are discussed.

• 公益社団法人 日本化学会の論文

著者

• Noyori Ryoji

  Department Of Chemistry And Molecular Chirality Research Unit Nagoya University

• Yamakawa Masashi

  Department of Chemistry, Nagoya University

• Takaya Hidemasa

  Chemical Materials Center, Institute for Molecular Science

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