Stereoselective synthesis of bicyclo[3.1.1]heptane derivatives via intramolecular photocycloaddition reaction |
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| Authors: | Honda Kiyoshi Konishi Mari Kawai Manabu Yamada Akihisa Takahashi Yasuhiko Hoshino Yujiro Inoue Seiichi |
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| Affiliation: | Graduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai 79-5, Hodogaya-ku, Yokohama 240-8501, Japan. k-honda@ynu.ac.jp |
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| Abstract: | Optically active 1,3-bridged cyclobutanes 10 of the bicyclo[3.1.1]heptane ring system and 1,2-bridged cyclobutanes 11 of the bicyclo[3.2.0]heptane ring system were produced by UV irradiation of alpha,beta,gamma,delta-unsaturated esters 9a and 9c-f. The preference of endo-stereochemistry at C-6 bridged head was observed in cross-adducts 10. On the other hand, irradiation of conjugated dienol 9b led via only parallel cycloaddition to 1,2-bridged cyclobutane 11. |
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