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Amidation of esters with amino alcohols using organobase catalysis

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

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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.