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Synthesis and evaluation of a chiral menthol functionalized silsesquioxane: application to diastereoselective [2+2] photocycloaddition |
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| Authors: | Yuuki Yanagisawa Hiroki Yamaguchi Yasuhiro Nishiyama Tsumoru Morimoto Kiyomi Kakiuchi Kenji Tabata Ken Tsutsumi |
| Affiliation: | 1. Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara, 630-0192, Japan 2. Department of Applied Chemistry, Faculty of Engineering, Miyazaki University, 1-1 Gakuen Kibanadai-Nishi, Miyazaki, 889-2155, Japan |
| Abstract: | A novel chiral menthol derivative supported on silsesquioxane was easily synthesized by hydrosilylation of the corresponding arylmenthyl olefin with commercially available silsesquioxane-type hydrosilane. We evaluated the applicability of the silsesquioxane-based compound to diastereoselective [2+2] photocycloaddition reaction. The newly synthesized silsesquioxane-based chiral menthol derivative 9 indicated similar diastereoselectivity to the corresponding p-methoxyphenyl menthol derivative. |
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