20030-44-8Relevant articles and documents
An enantioselective synthesis of (R)-2-amino-1-hydroxyethylphosphonic acid by hydrolytic kinetic resolution of (±)-diethyl oxiranephosphonate
Wyatt, Peter B.,Blakskjaer, Peter
, p. 6481 - 6483 (2007/10/03)
(±)-Diethyl oxiranephosphonate undergoes efficient hydrolytic kinetic resolution by (R,R)-N,N'-bis(3,5-di-tertbutylsalicylidene)-1,2- cyclohexanediaminocobalt(III) acetate; opening of the resultant (R)-epoxide by benzylamine, followed by phosphonate ester hydrolysis and hydrogenolysis, affords the protozoal plasma membrane component (R)-2-amino-1- hydroxyethylphosphonic acid.
ETUDE DE LA REACTION DE CYCLISATION DES HALOHYDRINES-1,2 ETHYL PHOSPHONATES DE DIETHYLE POUR L'OBTENTION DE L'EPOXY-1,2 ETHYL PHOSPHONATE DE DIETHYLE
Sturtz, G.,Pondaven-Raphalen, A.
, p. 35 - 48 (2007/10/02)
Here we report on the synthesis of the diethyl 1,2-epoxyethylphosphonate 1 from diethyl 1-halogeno 2-hydroxyethylphosphonates 4a and 4b.The halohydrins were prepared by hypohalogenation of the diethyl vinylphosphonate and their structures confirmed by 31P, 1H and 13C NMR spectroscopy.The epoxidation cyclisation was studied using a variety of bases (HNa, KOH, EtO-, K2CO3) and solvents (THF, EtOH, MeOH).In aprotic solvents, there was a competition between the epoxidation cyclisation and a Wittig-Horner type reaction leading to the vinyl chloride.Good yields of the title compound 1 were obtained using the phase transfer catalysed reactions conditions.