Amidation of esters with amino alcohols using organobase catalysis

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

doi:10.1021/jo501929c

Amidation of esters with amino alcohols using organobase catalysis

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

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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 language	English
Pages (from-to)	9347-9354
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	79
Issue number	19
Early online date	7 Sept 2014
DOIs	https://doi.org/10.1021/jo501929c
Publication status	Published - 3 Oct 2014

Keywords

amino alcohol
dimethyl carbonate
unactivated esters

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10.1021/jo501929c

Jamieson-etal-JOC2014-amino-alcohols-using-organobase-catalysisAccepted author manuscript, 1 MB

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title = "Amidation of esters with amino alcohols using organobase catalysis",

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.",

keywords = "amino alcohol, dimethyl carbonate, unactivated esters",

author = "Nicola Caldwell and Campbell, {Peter S.} and Craig Jamieson and Frances Potjewyd and Iain Simpson and Watson, {Allan J. B.}",

note = "This document is the unedited author's version of a Submitted Work that was subsequently accepted for publication in Journal of Organic Chemistry, copyright {\textcopyright} American Chemical Society after peer review. To access the final edited and published work, see http://pubs.acs.org/doi/abs/10.1021/jo501929c.",

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T1 - Amidation of esters with amino alcohols using organobase catalysis

AU - Caldwell, Nicola

AU - Campbell, Peter S.

AU - Jamieson, Craig

AU - Potjewyd, Frances

AU - Simpson, Iain

AU - Watson, Allan J. B.

N1 - 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.

PY - 2014/10/3

Y1 - 2014/10/3

N2 - 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.

AB - 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.

KW - amino alcohol

KW - dimethyl carbonate

KW - unactivated esters

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UR - http://pubs.acs.org/journal/joceah

U2 - 10.1021/jo501929c

DO - 10.1021/jo501929c

M3 - Article

AN - SCOPUS:84907801844

SN - 0022-3263

VL - 79

SP - 9347

EP - 9354

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Amidation of esters with amino alcohols using organobase catalysis

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