Attempts at asymmetric electrosynthesis of alpha-fluorinated cyclopropylphosphonamides

Citation
S. Goumain et al., Attempts at asymmetric electrosynthesis of alpha-fluorinated cyclopropylphosphonamides, J CHEM S P1, (7), 2001, pp. 701-705
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
7
Year of publication
2001
Pages
701 - 705
Database
ISI
SICI code
1472-7781(2001):7<701:AAAEOA>2.0.ZU;2-5
Abstract
Variously N,N-disubstituted chiral dibromofluoromethylphosphonamides 3 were easily prepared and used for the asymmetric electrosynthesis, in the prese nce of tert-butyl acrylate, of alpha -fluorinated cyclopropylphosphonamides 7. The diastereoisomeric excesses are moderate (up to 40%). Moreover, the identification of the trans and cis stereoisomers has been deduced from ana lysis of 2D H-1-F-19 HOESY spectra.