Journal
ELECTROCHIMICA ACTA
Volume 54, Issue 5, Pages 1638-1644Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.electacta.2008.09.057
Keywords
Chiral auxiliaries; Ionic liquid; Electrochemistry; Oxazolidin-2-ones; Acylation
Categories
Funding
- MURST (Prin 2006)
- CNR, Rome, Italy
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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-1H-imidazol-2-ylidene) has been indicated as the base involved in the deprotonation of chiral oxazolidin-2-ones. (c) 2008 Elsevier Ltd. All rights reserved.
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