Fluoroaziridines as novel substrates in the modified Petasis reaction: synthesis of monofluorinated propargyl amines

Reaction of 2-fluoroaziridines with potassium alkynyltrifluoroborates in the presence of BF3·OEt2 leads to fluorinated propargyl amines in moderate to good yields. The reaction proceeds as an in situ isomerization of 2-fluoroaziridines to α-fluorinated imines, followed by the reaction of the imine w...

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Bibliographic Details
Published in:Tetrahedron 2008-01, Vol.64 (1), p.117-123
Main Authors: Konev, Alexander S., Stas, Sara, Novikov, Mikhail S., Khlebnikov, Alexander F., Abbaspour Tehrani, Kourosch
Format: Article
Language:English
Subjects:
Boron
Fluorinated aldimines
Fluorinated amines
Fluoroaziridines
Petasis
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Summary:Reaction of 2-fluoroaziridines with potassium alkynyltrifluoroborates in the presence of BF3·OEt2 leads to fluorinated propargyl amines in moderate to good yields. The reaction proceeds as an in situ isomerization of 2-fluoroaziridines to α-fluorinated imines, followed by the reaction of the imine with alkynyldifluoroborane, which is generated in situ from the potassium alkynyltrifluoroborates and BF3·OEt2. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.10.067