α-Heteroarylation of Ketones via the Umpolung Reaction of N-Alkoxyenamine

Tetsuya Miyoshi; Norihiko Takeda; Masaki Fukami; Shohei Sato; Masafumi Ueda; Okiko Miyata

doi:10.1248/cpb.c14-00404

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α-Heteroarylation of Ketones via the Umpolung Reaction of N-Alkoxyenamine

Tetsuya Miyoshi, Norihiko Takeda, Masaki Fukami, Shohei Sato, Masafumi Ueda, Okiko Miyata

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Keywords: umpolung, heteroarylation, N-alkoxyenamine, aluminum

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2014 Volume 62 Issue 9 Pages 927-932

DOI https://doi.org/10.1248/cpb.c14-00404

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Abstract

A new method has been developed for the umpolung α-heteroarylation of ketones via an N-alkoxyenamine. The treatment of ketones with tris(heteroaryl)aluminum reagents in the presence of isoxazolidine gave the corresponding α-heteroarylated ketones in moderate to good yields.

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