Synthesis of phosphinates, structural phosphoryl analogs of putrescine andspermidine

Authors
Mortier, J Fortineau, AD Vaultier, M
Citation
J. Mortier et al., Synthesis of phosphinates, structural phosphoryl analogs of putrescine andspermidine, PHOSPHOR SU, 149, 1999, pp. 221-228
Citations number
21
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
ISSN journal
10426507 → ACNP
Volume
149
Year of publication
1999
Pages
221 - 228
Database
ISI
SICI code
1042-6507(1999)149:<221:SOPSPA>2.0.ZU;2-L
Abstract
The phosphinates 1 and 2, phosphorylated analogues of putrescine and spermi dine. were synthesized from a common precursor. ethyl(phtalimidomethyl)viny lphosphinate (9) by monochlorination of diethyl(phtalimidomethyl)phosphonat e (7) and subsequent treatment with vinylmagnesium bromide. Michael additio n of benzylamine or 3-azidopropylamine to 9 followed by catalytic hydrogena tion (Pd/C) afforded 1 and 2 in good overall yields.