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

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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Bibliographische Detailangaben
Veröffentlicht in:	Chemical & pharmaceutical bulletin 2014/09/01, Vol.62(9), pp.927-932
Hauptverfasser:	Miyoshi, Tetsuya, Takeda, Norihiko, Fukami, Masaki, Sato, Shohei, Ueda, Masafumi, Miyata, Okiko
Format:	Artikel
Sprache:	eng
Schlagworte:	aluminum heteroarylation Heterocyclic Compounds - chemistry Hydrocarbons - chemistry Ketones - chemistry Magnetic Resonance Spectroscopy N-alkoxyenamine Spectrometry, Mass, Electrospray Ionization Spectroscopy, Fourier Transform Infrared umpolung
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Beschreibung
Zusammenfassung:	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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.c14-00404