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An Iridium-Catalyzed Reductive Approach to Nitrones from N-Hydroxyamides

Seiya Katahara, Shoichiro Kobayashi, Kanami Fujita, Tsutomu Matsumoto, Takaaki Sato* and Noritaka Chida*

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan, Email: takaakisapplc.keio.ac.jp, chidaapplc.keio.ac.jp

S. Katahara, S. Kobayashi, K. Fujita, T. Matsumoto, T. Sato, N. Chida, J. Am. Chem. Soc., 2016, 138, 5246-5249.

DOI: 10.1021/jacs.6b02324 (free Supporting Information)


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Abstract

An Ir-catalyzed reductive formation of functionalized nitrones from N-hydroxyamides via dehydrosilylation and hydrosilylation showed high chemoselectivity in the presence of sensitive functional groups, such as methyl esters. The reaction was successfully applied to the synthesis of cyclic and macrocyclic nitrones, which are known to be challenging compounds.

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Key Words

Nitrones, Silanes


ID: J48-Y2016