Addition of one equivalent of dialkylphosphite to γ-diketones yielded new 5-phosphorylated 1-pyrrolines 3. Depending on the experimental conditions, the addition of a second equivalent of dialkylphosphite to 3, led either to (+/-)-2,5-bis-phosphorylated pyrrolidines 4 or a mixture of (+/-)- and meso-4. Pyrrolidines 4 were isolated and subsequently oxidized to the corresponding stable (+/-)- or meso-nitroxides, 5. Coupling of (+/-)-5a with the prochiral 2-phenyl-ethyl radical was investigated.
L'addition d'un equivalent de phosphite dialkylique a des γ-dicetones a conduit a de nouvelles 1-pyrrolines phosphorylees en position 5, 3. Suivant les conditions experimentales, l'addition a 3 d'un deuxieme equivalent de phosphite dialkylique a fourni soit des (+/-)- pyrrolidines 2,5- diphosphorylees, (+/-)-4, soit des meso-4. Celles-ci ont ete facilement oxydees pour conduire aux nitroxydes stables correspondants, 5. Le couplage de (+/-)-5a avec le radical prochiral 2-phenyl-ethyle a ete etudie.