One-pot method for α-phenylation of ketones using isoxazolidine and triphenylaluminum

T Miyoshi, S Sato, H Tanaka, C Hasegawa, M Ueda…

Index: Miyoshi, Tetsuya; Sato, Shohei; Tanaka, Hiroya; Hasegawa, Chihiro; Ueda, Masafumi; Miyata, Okiko Tetrahedron Letters, 2012 , vol. 53, # 32 p. 4188 - 4191

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Abstract

The efficient one-pot umpolung α-phenylation of ketones via N-alkenylisoxazolidine is described. When the various ketones are treated with triphenylaluminum prepared from phenylmagnesium chloride and AlCl3 in the presence of isoxazolidine, the desired products are obtained in good to moderate yield. This method is equivalent to a direct α-arylation reaction of carbonyl groups.