Electrogenerated N-heterocyclic carbene: N-acylation of chiral oxazolidin-2-ones in ionic liquids |
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Authors: | Isabella Chiarotto |
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Affiliation: | Dipartimento Ingegneria Chimica Materiali Ambiente, Università “La Sapienza”, via Castro Laurenziano, 7, 00161 Roma, Italy |
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Abstract: | An electrochemical procedure for the N-acylation of chiral oxazolidin-2-ones, in the absence of volatile molecular organic solvents, has been set up via electrolyses of ionic liquid [bmim]BF4 containing oxazolidin-2-ones followed by addition of saturated or unsaturated anhydrides. N-acyloxazolidin-2-ones were isolated in good to elevated yields. The electrochemically induced N-acylation of chiral oxazolidin-2-ones occurs with total retention of the absolute configuration of all the chiral atoms. The electrogenerated carbene (1-butyl-3-methyl-1H-imidazol-2-ylidene) has been indicated as the base involved in the deprotonation of chiral oxazolidin-2-ones. |
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Keywords: | Chiral auxiliaries Ionic liquid Electrochemistry Oxazolidin-2-ones Acylation |
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