Amidation of esters with amino alcohols using organobase catalysis

Nicola Caldwell, Peter S. Campbell, Craig Jamieson, Frances Potjewyd, Iain Simpson, Allan J. B. Watson

Research output: Contribution to journalArticle

25 Citations (Scopus)
126 Downloads (Pure)

Abstract

A catalytic protocol for the base-mediated amidation of unactivated esters with amino alcohol derivatives is reported. Investigations into mechanistic aspects of the process indicate that the reaction involves an initial transesterification, followed by an intramolecular rearrangement. The reaction is highly general in nature and can be extended to include the synthesis of oxazolidinone systems through use of dimethyl carbonate.

Original languageEnglish
Pages (from-to)9347-9354
Number of pages8
JournalJournal of Organic Chemistry
Volume79
Issue number19
Early online date7 Sep 2014
DOIs
Publication statusPublished - 3 Oct 2014

Keywords

  • amino alcohol
  • dimethyl carbonate
  • unactivated esters

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