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Catalytic Synthesis of Saturated Oxygen Heterocycles by Hydrofunctionalization of Unactivated Olefins: Unprotected and Protected Strategies

Hiroki Shigehisa*, Miki Hayashi, Haruna Ohkawa, Tsuyoshi Suzuki, Hiroki Okayasu, Mayumi Mukai, Ayaka Yamazaki, Ryohei Kawai, Harue Kikuchi, Yui Satoh, Akane Fukuyama, and Kou Hiroya

*Faculty of Pharmacy, Musashino University, 1-1-20 Shinmachi Nishitokyo-shi, Tokyo 202-8585, Japan, Email: cgehisamusashino-u.ac.jp

H. Shigehisa, M. Hayashi, H. Ohkawa, T. Suzuki, H. Okayasu, M. Mukai, A. Yamazaki, R. Kawai, H. Kikuchi, Y. Satoh, A. Fukuyama, K. Hiroya, J. Am. Chem. Soc., 2016, 138, 10084-10087.

DOI: 10.1021/jacs.6b05720 (free Supporting Information)


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Abstract

A mild, general, and functional group tolerant intramolecular hydroalkoxylation and hydroacyloxylation of unactivated olefins using a Co(salen) complex, an N-fluoropyridinium salt, and a disiloxane reagent at room temperature provides five- and six-membered cyclic ethers and lactones. The powerful Co catalyst system also enables the deprotective hydroalkoxylation of O-protected alkenyl alcohol and hydroacyloxylation of alkenyl esters.

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Key Words

tetrahydrofurans, tetrahydropyrans, lactones


ID: J48-Y2016