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Synthesis and evaluation of a chiral menthol functionalized silsesquioxane: application to diastereoselective [2+2] photocycloaddition

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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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Acknowledgments

This work was supported partially by a Grant-in Aid for Scientific Research (B) No. 21310081 and for Research on Innovative areas “Organic Synthesis Based on Reaction Integration. Development of New Methods and Creation of New Substances” (No. 2105) No. 22106532 from the Ministry of Education, Culture, Sports, Science and Technology of the Japanese Government (MEXT), and a grant-in-aid for scientific research from Nara Institute of Science and Technology (NAIST). We thank Mr. F. Asanoma for his assistance in 1H NMR spectroscopy, and Ms. Y. Nishiyama and Ms. M. Yamamura for their help in TOF–MS measurements.

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Authors and Affiliations

  1. Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara, 630-0192, Japan

    Yuuki Yanagisawa, Hiroki Yamaguchi, Yasuhiro Nishiyama, Tsumoru Morimoto & Kiyomi Kakiuchi

  2. Department of Applied Chemistry, Faculty of Engineering, Miyazaki University, 1-1 Gakuen Kibanadai-Nishi, Miyazaki, 889-2155, Japan

    Kenji Tabata & Ken Tsutsumi

Authors
  1. Yuuki Yanagisawa
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  2. Hiroki Yamaguchi
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  3. Yasuhiro Nishiyama
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  4. Tsumoru Morimoto
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  5. Kiyomi Kakiuchi
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  6. Kenji Tabata
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  7. Ken Tsutsumi
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Correspondence to Kiyomi Kakiuchi.

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Yanagisawa, Y., Yamaguchi, H., Nishiyama, Y. et al. Synthesis and evaluation of a chiral menthol functionalized silsesquioxane: application to diastereoselective [2+2] photocycloaddition. Res Chem Intermed 39, 101–110 (2013). https://doi.org/10.1007/s11164-012-0635-5

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  • DOI: https://doi.org/10.1007/s11164-012-0635-5

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