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Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

Yoshito Takahashi, Risa Yoshii, Takaaki Sato*, 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

Y. Takahashi, R. Yoshii, T. Sato, N. Chida, Org. Lett., 2018, 20, 5705-5708.

DOI: 10.1021/acs.orglett.8b02421 (free Supporting Information)


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Abstract

After an iridium-catalyzed reduction of secondary amides, the resulting imines can undergo the Strecker reaction, the Mannich reaction, allylation, and [3 + 2]-cycloaddition. The method shows high chemoselectivity in the presence of other functional groups such as methyl ester.

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Key Words

α-aminonitriles, Strecker synthesis, diethylsilane


ID: J54-Y2018