Asymmetric induction in an intramolecular [2+2] photocycloaddition within chirally modified zeolite supercages |
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| Authors: | Hajime Maeda Takahiro Okumura Yasuharu Yoshimi Kazuhiko Mizuno |
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| Affiliation: | 1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan;2. Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Fukui University, 3-9-1 Bunkyo, Fukui, Fukui 910-8507, Japan |
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| Abstract: | Photoirradiation of 1-cyano-2-(5-methyl-2-oxa-4-hexenyl)naphthalene, included in NaY zeolites along with chiral inductors, such as diethyl tartrate or phenylalaninol, gives an intramolecular [2+2] photocycloadduct with a maximum 15% ee. The degree of enantioselectivity was found to depend on the Si/Al ratio, the nature of the cations in the zeolites, the structure of the chiral inductors, and the molar ratio of substrate and chiral inductors. |
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