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.
authors.affiliation: Department of Pure and Applied Chemistry, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, U.K.
authors.forename: Nicola
authors.initials: N
authors.lastname: Caldwell
authors.forename: Peter S
authors.initials: PS
authors.lastname: Campbell
authors.forename: Craig
authors.initials: C
authors.lastname: Jamieson
authors.forename: Frances
authors.initials: F
authors.lastname: Potjewyd
authors.forename: Iain
authors.initials: I
authors.lastname: Simpson
authors.forename: Allan J B
authors.initials: AJ
authors.lastname: Watson
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D005561:Formates / Q000737:chemistry; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis*
chemical_list: D000605:Amino Alcohols; D004952:Esters; D005561:Formates; D023303:Oxazolidinones; C023025:methyl carbonate