Amidation of esters with amino alcohols using organobase catalysis

Tools

Caldwell, Nicola and Campbell, Peter S. and Jamieson, Craig and Potjewyd, Frances and Simpson, Iain and Watson, Allan J. B. (2014) Amidation of esters with amino alcohols using organobase catalysis. Journal of Organic Chemistry, 79 (19). pp. 9347-9354. ISSN 0022-3263 (https://doi.org/10.1021/jo501929c)

[thumbnail of Jamieson-etal-JOC2014-amino-alcohols-using-organobase-catalysis]
Preview
 PDF. Filename: Jamieson_etal_JOC2014_amino_alcohols_using_organobase_catalysis.pdf
Accepted Author Manuscript
Download (1MB)| Preview

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.

ORCID iDs

Caldwell, Nicola, Campbell, Peter S. ORCID logoORCID: https://orcid.org/0000-0001-8981-186X, Jamieson, Craig ORCID logoORCID: https://orcid.org/0000-0002-6567-8272, Potjewyd, Frances ORCID logoORCID: https://orcid.org/0000-0003-4241-9873, Simpson, Iain and Watson, Allan J. B.;
  • Item type:Article
    ID code:52254
    Dates:
    Date
    Event
    3 October 2014
    Published
    7 September 2014
    Published Online
    7 September 2014
    Accepted
    Notes:This document is the unedited author's version of a Submitted Work that was subsequently accepted for publication in Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work, see http://pubs.acs.org/doi/abs/10.1021/jo501929c.
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:18 Mar 2015 16:25
    Last modified:16 Dec 2024 03:57
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/52254
CORE (COnnecting REpositories)