Issue 7, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Attempts at asymmetric electrosynthesis of α-fluorinated cyclopropylphosphonamides

Sophie Goumain,a   Hassan Oulyadi,b   Philippe Jubault,a   Christian Feassona  and  Jean-Charles Quiriona  

a Laboratoire d’Hétérochimie Organique, INSA de Rouen, IRCOF, 1 rue Tesnière, Mont-Saint-Aignan Cedex, France

b Laboratoire de Chimie Organique et Biologie Structurale de l’IRCOF, Université de Rouen, 1 rue Tesnière, Mont-Saint-Aignan Cedex, France

Abstract

Variously N,N-disubstituted chiral dibromofluoromethylphosphonamides 3 were easily prepared and used for the asymmetric electrosynthesis, in the presence of tert-butyl acrylate, of α-fluorinated cyclopropylphosphonamides 7. The diastereoisomeric excesses are moderate (up to 40%). Moreover, the identification of the trans and cis stereoisomers has been deduced from analysis of 2D 1H–19F HOESY spectra.

Graphical abstract: Attempts at asymmetric electrosynthesis of α-fluorinated cyclopropylphosphonamides

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Article information

DOI
https://doi.org/10.1039/B008906K
Article type
Paper
Submitted
06 Nov 2000
Accepted
19 Feb 2001
First published
14 Mar 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 701-705

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Attempts at asymmetric electrosynthesis of α-fluorinated cyclopropylphosphonamides

S. Goumain, H. Oulyadi, P. Jubault, C. Feasson and J. Quirion, J. Chem. Soc., Perkin Trans. 1, 2001, 701 DOI: 10.1039/B008906K

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