Conversion of Racemic Alkyl Aryl Sulfoxides into Pure Enantiomers Using a Recycle Photoreactor: Tandem Use of Chromatography on Chiral Support and Photoracemization on Solid Support.

Autor:	Tozawa K; 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., Tanaka Y; Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan., Nakamura K; Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan., Inagaki A; Faculty of Science and Technology, Seikei University, 3-3-1 Kichijoji Kitamachi, Musashino-shi, Tokyo 180-8633, 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 Co., Ltd., 284 Daigo, Karasuma Nishiiru Gojo-dori, Shimogyo-ku, Kyoto 600-8106, Japan., Kanemaru K; IWASAKI ELECTRIC CO., LTD., 1-1, Ichiriyama-cho, Gyoda-shi, Saitama 361-8505, Japan., Oda Y; IWASAKI ELECTRIC CO., LTD., 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] 2023 Jun 02; Vol. 88 (11), pp. 6955-6961. Date of Electronic Publication: 2023 May 08.
DOI:	10.1021/acs.joc.3c00265
Abstrakt:	Chiral sulfoxides are valuable in the fields of medicinal chemistry and organic synthesis. A recycle photoreactor utilizing the concept of deracemization, where a racemate is converted into a pure enantiomer, is developed and successfully applied in the syntheses of chiral alkyl aryl sulfoxides. The recycling system consists of rapid photoracemization using an immobilized photosensitizer and separation of the enantiomers via chiral high-performance liquid chromatography, and the desired pure chiral sulfoxides are obtained after 4-6 cycles. The key to the success of the system is the photoreactor site, wherein the photosensitizer 2,4,6-triphenylpyrylium is immobilized on the resin and irradiated (405 nm) to enable the rapid photoracemizations of the sulfoxides. As the green recycle photoreactor requires no chiral components, it should be a useful alternative system for application in producing chiral compounds.
Databáze:	MEDLINE
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