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

23 Citations (Scopus)

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.

LanguageEnglish
Pages9347-9354
Number of pages8
JournalJournal of Organic Chemistry
Volume79
Issue number19
Early online date7 Sep 2014
DOIs
Publication statusPublished - 3 Oct 2014

Fingerprint

Amino Alcohols
Oxazolidinones
Transesterification
Catalysis
Esters
Derivatives
methyl carbonate

Keywords

  • amino alcohol
  • dimethyl carbonate
  • unactivated esters

Cite this

Caldwell, N., Campbell, P. S., Jamieson, C., Potjewyd, F., Simpson, I., & Watson, A. J. B. (2014). Amidation of esters with amino alcohols using organobase catalysis. Journal of Organic Chemistry, 79(19), 9347-9354. https://doi.org/10.1021/jo501929c
Caldwell, Nicola ; Campbell, Peter S. ; Jamieson, Craig ; Potjewyd, Frances ; Simpson, Iain ; Watson, Allan J. B. / Amidation of esters with amino alcohols using organobase catalysis. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 19. pp. 9347-9354.
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Caldwell, N, Campbell, PS, Jamieson, C, Potjewyd, F, Simpson, I & Watson, AJB 2014, 'Amidation of esters with amino alcohols using organobase catalysis' Journal of Organic Chemistry, vol. 79, no. 19, pp. 9347-9354. https://doi.org/10.1021/jo501929c

Amidation of esters with amino alcohols using organobase catalysis. / Caldwell, Nicola; Campbell, Peter S.; Jamieson, Craig; Potjewyd, Frances; Simpson, Iain; Watson, Allan J. B.

In: Journal of Organic Chemistry, Vol. 79, No. 19, 03.10.2014, p. 9347-9354.

Research output: Contribution to journalArticle

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Caldwell N, Campbell PS, Jamieson C, Potjewyd F, Simpson I, Watson AJB. Amidation of esters with amino alcohols using organobase catalysis. Journal of Organic Chemistry. 2014 Oct 3;79(19):9347-9354. https://doi.org/10.1021/jo501929c