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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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
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container_end_page 932
container_issue 9
container_start_page 927
container_title Chemical & pharmaceutical bulletin
container_volume 62
creator Miyoshi, Tetsuya
Takeda, Norihiko
Fukami, Masaki
Sato, Shohei
Ueda, Masafumi
Miyata, Okiko
description 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.
doi_str_mv 10.1248/cpb.c14-00404
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subjects aluminum
heteroarylation
Heterocyclic Compounds - chemistry
Hydrocarbons - chemistry
Ketones - chemistry
Magnetic Resonance Spectroscopy
N-alkoxyenamine
Spectrometry, Mass, Electrospray Ionization
Spectroscopy, Fourier Transform Infrared
umpolung
title α-Heteroarylation of Ketones via the Umpolung Reaction of N-Alkoxyenamine
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