Cermak, Diana M.; Du, Yanming; Wiemer, David F. published the artcile< Synthesis of Nonracemic Dimethyl α-(Hydroxyfarnesyl)phosphonates via Oxidation of Dimethyl Farnesylphosphonate with (Camphorsulfonyl)oxaziridines>, Category: isothiazole, the main research area is hydroxyfarnesylphosphonate preparation oxidation camphorsulfonyloxaziridine stereoselective.
Several strategies for synthesis of nonracemic di-Me α-(hydroxyfarnesyl)phosphonate and the parent phosphonic acid have been explored. Separation of diastereomeric derivatives prepared by esterification of racemic α-hydroxy phosphonate with (S)-(+)-O-methylmandelic acid was possible, and these diastereomers could be assigned absolute stereochem. on the basis of literature precedent. However, hydrolysis to the α-hydroxy phosphonic acid was accompanied by extensive isomerization. Addition of a nonracemic phosphonamidite to farnesal also gave nonracemic material, but again hydrolysis was problematic. Oxidation of di-Me farnesylphosphonate anion with nonracemic (camphorsulfonyl)oxaziridines was shown to be regio- and stereoselective for formation of the α-hydroxy phosphonate. Enantiomeric excess of ∼70% ee was established by conversion of the oxidation products to their (S)-(+)-O-methylmandelate derivatives Although hydrolysis of these Me esters was accompanied by extensive racemization, both enantiomers of α-(hydroxyfarnesyl)phosphonic acid were obtained in low ee by this strategy.
Journal of Organic Chemistry published new progress about Selective oxidation (regio- and stereoselective). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Category: isothiazole.
Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com