W(CO)_5(L)-Catalyzed Construction of Cyclic Carbon Frameworks

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概要

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• Several novel reactions are developed utilizing the electron-deficient nature of terminal alkyne-W (CO) <SUB>5</SUB> π-complexes and/or their isomerized vinylidene complexes. Terminal alkynes having a silyl enol ether moiety in the molecule undergo <I>endo</I>-selective cyclization using a catalytic amount of W (CO) <SUB>5</SUB> (thf). In some cases, both <I>exo</I>-and <I>endo</I>-selective cyclizations are achieved depending on the reaction conditions. Iodinated vinylidene intermediates are generated from the corresponding iodoalkynes and W (CO) <SUB>5</SUB> (thf), and are employed for the related cyclizations. Electrocyclization of <I>o</I>-ethynylphenyl ketones gives novel benzopyranylidene complexes, which undergo Diels-Alder reaction with electron-rich alkenes to give substituted naphthalenes. Furthermore, the reaction of <I>o</I>-ethynylphenyl ketones and electron-rich alkenes in the presence of a catalytic amount of W (CO) <SUB>5</SUB> (thf) proceeds through the novel tungsten-containing carbonyl ylides, which react with the electron-rich alkenes in a [3+2] -cycloaddition manner to give polycyclic compounds.

• 社団法人 有機合成化学協会の論文
• 2002-11-01

著者

• MAEYAMA Katsuya

  Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology

• Maeyama Katsuya

  Department Of Chemistry Tokyo Institute Of Technology

• IWASAWA Nobuharu

  Department of Chemistry, Faculty of Science, The University of Tokyo

• KUSAMA Hiroyuki

  Department of Chemistry, Graduate School of Science, The University of Tokyo

• Kusama Hiroyuki

  Department Of Chemistry Graduate School Of Science The University Of Tokyo

• Iwasawa Nobuharu

  Department Of Chemistry Faculty Of Science The University Of Tokyo

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