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1. Photochemical addition of cyclic ethers/acetals to olefins using BuOO Bu: Synthesis of masked ketones/aldehydes and diols

Author

Kou Uchida, Chuanxiang Liu, Rina Shimizu, Ryuusei Yamada, Yoshiki Wakame, Hisashi Shirota, Tadashi Aoyama, Hajime Omori, Mamiko Hayakawa, Akihiko Ouchi, Han Xu, Hiroshi Mashimo, and Seiya Niino

Subjects
010405 organic chemistry, Organic Chemistry, Bond formation, 010402 general chemistry, Photochemistry, 01 natural sciences, Biochemistry, Peroxide, 0104 chemical sciences, Hydrolysis, chemistry.chemical_compound, chemistry, Yield (chemistry), Drug Discovery
Abstract

A fast photochemical C–C bond formation between cyclic ethers/acetals and olefins using di-tert-butyl peroxide (DTBP) was developed. This method provides easy access to 2-substituted cyclic ethers, and 2- or 4-substituted cyclic acetals. Acyl/formyl groups or diols can be obtained by the hydrolysis of the 2- or 4-substituted cyclic acetals, respectively. The reactions proceeded at room temperature and gave the expected products in good to excellent yields; efficient reactions were completed within 0.5 h at room temperature in >95% yield.

Published
2020

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