A new synthesis of N -enoyloxazolidin-2-ones has been performed by electrochemical reduction of ,-di- and trichloroketones in aprotic solvent in the presence of Evans’ chiral auxiliaries (oxazolidin-2-ones). The electrochemical reduction of trichloroke- tones via a chlorocyclopropanone as intermediate allows a Favorskii rearrangement involving trichloroketones and oxazolidin-2- ones. N -Enoyloxazolidin-2-ones have been obtained this way under mild reaction conditions and in good to high yields.
An efficient electrochemical method for N-acryloylation of oxazolidin-2-ones chiral auxiliaries with alpha,alpha'-polyhaloketones / Feroci, Marta; Inesi, Achille; M., Orsini; L., Rossi; G., Sotgiu. - In: JOURNAL OF ELECTROANALYTICAL CHEMISTRY. - ISSN 1572-6657. - STAMPA. - 507(1-2):(2001), pp. 89-95. [10.1016/S0022-0728(01)00411-9]
An efficient electrochemical method for N-acryloylation of oxazolidin-2-ones chiral auxiliaries with alpha,alpha'-polyhaloketones
FEROCI, Marta;INESI, ACHILLE;
2001
Abstract
A new synthesis of N -enoyloxazolidin-2-ones has been performed by electrochemical reduction of ,-di- and trichloroketones in aprotic solvent in the presence of Evans’ chiral auxiliaries (oxazolidin-2-ones). The electrochemical reduction of trichloroke- tones via a chlorocyclopropanone as intermediate allows a Favorskii rearrangement involving trichloroketones and oxazolidin-2- ones. N -Enoyloxazolidin-2-ones have been obtained this way under mild reaction conditions and in good to high yields.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
