Isomerization of E -Cinnamamides into Z -Cinnamamides Using a Recycling Photoreactor.

Autor: Suga M; Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan., Fukushima S; Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan., Makino K; Research Institute of Pharmaceutical Sciences, Musashino University, Nishitokyo, Tokyo 202-8585, Japan., Nakamura K; Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan., Tabata H; Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan., Oshitari T; Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan., Natsugari H; Graduate School of Pharmaceutical Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan., Kuroda N; YMC Company Limited, 284 Daigo, Karasuma Nishiiru Gojo-dori, Shimogyo-ku, Kyoto 600-8106, Japan., Kanemaru K; IWASAKI Electric Company Limited, 1-1, Ichiriyama-cho, Gyoda-shi, Saitama 361-8505, Japan., Oda Y; IWASAKI Electric Company Limited, 1-1, Ichiriyama-cho, Gyoda-shi, Saitama 361-8505, Japan., Takahashi H; Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Jun 21; Vol. 89 (12), pp. 8836-8844. Date of Electronic Publication: 2024 Jun 05.
DOI: 10.1021/acs.joc.4c00721
Abstrakt: The photocatalytic synthesis of thermodynamically less-stable Z -alkenes has received considerable research attention in recent years. In this study, a recycling photoreactor was applied to the photoisomerization of E -alkenes (cinnamamide and Weinreb amide derivatives) to produce Z -alkenes. The closed-loop recycling system comprises an immobilized photosensitizer to achieve rapid photoisomerization and a high-performance liquid chromatography instrument for separation of the Z / E diastereomers. After 4-10 cycles, the desired pure Z -alkenes were obtained efficiently. In the photoreactor system, a photosensitizer (thioxanthone) was covalently immobilized on silica gel via amide bonding, which led to an enhanced photocatalytic activity compared to the parent thioxanthone. This recycling photoreactor shows promise as an alternative system for the production of Z -alkenes.
Databáze: MEDLINE
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