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Electrogenerated N-heterocyclic carbene:N-acylation of chiral oxazolidin-2-ones in ionic liquids

Authors
Journal
Electrochimica Acta
0013-4686
Publisher
Elsevier
Publication Date
Volume
54
Issue
5
Identifiers
DOI: 10.1016/j.electacta.2008.09.057
Keywords
  • Chiral Auxiliaries
  • Ionic Liquid
  • Electrochemistry
  • Oxazolidin-2-Ones
  • Acylation
Disciplines
  • Chemistry

Abstract

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]BF 4 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-1 H-imidazol-2-ylidene) has been indicated as the base involved in the deprotonation of chiral oxazolidin-2-ones.

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