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Synthesis 2009(7): 1087-1094  
DOI: 10.1055/s-0028-1087988
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Remarkable Access to γ-Fluoroalkylated Propargylamine Derivatives or Fluoroalkylated Dihydroisoxazoles via the Reaction of Fluoroalkylated Acetylides with Various Nitrones

Tsutomu Konno*, Kazuki Moriyasu, Takashi Ishihara
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan
Fax: +81(75)7247580; e-Mail: konno@chem.kit.ac.jp;
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Publication History

Received 4 November 2008
Publication Date:
06 March 2009 (online)

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Abstract

The reactions of fluoroalkylated acetylides with various nitrones were investigated. When nitrones with an alkyl substituent were employed, hydroxylamines were obtained in high yields, and smooth dehydroxylation followed, to give the corresponding propargylamines. Nitrones with an aryl substituent underwent nucleophilic addition and subsequent intramolecular cyclization, affording the corresponding fluoroalkylated dihydroisoxazoles in moderate yields. These sequences were also extended to chiral versions.

Key words

fluorine-containing compounds - propargylamines - nitrones - amines - heterocycles

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