A new synthesis of N-enoyloxazolidin-2-ones has been performed by electrochemical reduction of alpha,alpha'-di- and trichloroketones in aprotic solvent in the presence of Evans' chiral auxiliaries (oxazolidin-2-ones). The electrochemical reduction of trichloroketones 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-one chiral auxiliaries with alpha,alpha '-di- and trichloroketones

ROSSI, LEUCIO;
2001-01-01

Abstract

A new synthesis of N-enoyloxazolidin-2-ones has been performed by electrochemical reduction of alpha,alpha'-di- and trichloroketones in aprotic solvent in the presence of Evans' chiral auxiliaries (oxazolidin-2-ones). The electrochemical reduction of trichloroketones 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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11697/6321
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