Stereochemical study on 1,3-dipolar cycloaddition reactions of heteroaromatic N-ylides with symmetrically substituted cis and trans olefins.

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概要

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• Stereochemistry of the cycloadditions of twenty-four heteroaromatic <I>N</I>-ylides with several symmetrically substituted cis and trans olefins has been investigated. Cyclic and acyclic cis olefins cycloadd to the and form of the ylides in a highly <I>endo</I>-selective manner giving almost quantitative yields of stereospecific endo 3+2 cycloadducts. <I>N</I>-Ylides stabilized with a substituent of carbonyl type react with trans olefins to form mostly two stereoisomeric 3+2 cycloadducts to the anti form of the ylides. In most cases, they undergo the stereospecific interconversion through a retro cycloaddition process, the isomer ratios and the easiness of transformation depending upon the nature and size of substituents on the five-membered ring which has been built up in the cycloaddition step. On the other hand, <I>N</I>-ylides stabilized with a substituent of noncarbonyl type react with trans olefins to give stereospecific and stereoselective 3+2 cycloadducts as single isomers which are assigned as the cycloadducts to the syn form of the ylides.

• 公益社団法人 日本化学会の論文

著者

• Tsuge Otohiko

  Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences Kyushu University

• Takenaka Shigeori

  Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University

• Kanemasa Shuji

  Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Science, Kyushu University

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