The 1,3-dipolar cycloaddition reaction of N-alkyl nitrones with diphenylvinylphosphines affords directly isoxazolidinylphosphines in satisfactory yields and in regio- and stereoselective manner. The parent diphenylvinylphosphine was found to favor the formation of 5-phosphinoisoxazolidines whereas diphenylpropenylphosphine gave instead the 4-phosphinoisoxazolidine regioisomer. However, in reactions utilizing an alkylarylvinylphosphine and/or N-arylnitrone, oxidation of the phosphine by the nitrone reagent was found to precede the cycloaddition. An attempted conversion of the bicyclic isoxazolidine derived from 2,2-dimethyl-dihydro-2H-pyrrole 1-oxide and diphenylvinylphosphine to the perhydropyrrolo[1,2-c] [1,3,2]oxaza-phosphorine ring system was accomplished through the use of the corresponding phosphine oxide derivative and provided a single diastereoisomer of the desired pyrrolooxazaphosphorinane characterized ultimately in the form of its dioxide hydrate by the X-ray diffraction technique.
Direct Synthesis of Isoxazolidinylphosphines by Cycloaddition of Nitrones to Diphenylphosphinoethenes and X-Ray Structure of 7,7-Dimethyl-1-oxo-1-phenyl- 3-diphenylphosphinyl-hexahydropyrrolo[1,2-c]oxazaphosphorine / K. M. PIETRUSIEWICZ; I. SALAMONCZYK; W. WIECZOREK; A. BRANDI; S. CICCHI; A. GOTI. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 47:(1991), pp. 9083-9096. [10.1016/S0040-4020(01)86511-X]
Direct Synthesis of Isoxazolidinylphosphines by Cycloaddition of Nitrones to Diphenylphosphinoethenes and X-Ray Structure of 7,7-Dimethyl-1-oxo-1-phenyl- 3-diphenylphosphinyl-hexahydropyrrolo[1,2-c]oxazaphosphorine
BRANDI, ALBERTO;CICCHI, STEFANO;GOTI, ANDREA
1991
Abstract
The 1,3-dipolar cycloaddition reaction of N-alkyl nitrones with diphenylvinylphosphines affords directly isoxazolidinylphosphines in satisfactory yields and in regio- and stereoselective manner. The parent diphenylvinylphosphine was found to favor the formation of 5-phosphinoisoxazolidines whereas diphenylpropenylphosphine gave instead the 4-phosphinoisoxazolidine regioisomer. However, in reactions utilizing an alkylarylvinylphosphine and/or N-arylnitrone, oxidation of the phosphine by the nitrone reagent was found to precede the cycloaddition. An attempted conversion of the bicyclic isoxazolidine derived from 2,2-dimethyl-dihydro-2H-pyrrole 1-oxide and diphenylvinylphosphine to the perhydropyrrolo[1,2-c] [1,3,2]oxaza-phosphorine ring system was accomplished through the use of the corresponding phosphine oxide derivative and provided a single diastereoisomer of the desired pyrrolooxazaphosphorinane characterized ultimately in the form of its dioxide hydrate by the X-ray diffraction technique.I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.