title: Synthesis of tert-alkyl amino hydroxy carboxylic esters via an intermolecular ene-type reaction of oxazolones and enol ethers.
abstract: tert-Alkyl amino hydroxy carboxylic acids are abundantly present within the structure of many biologically active natural products. We describe herein the synthesis of these substrates using an oxazolone-mediated ene-type reaction with enol ethers followed by NaBH4 reduction of the intermediate oxazolone.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Mosey
authors.forename: Jason S
authors.initials: JS
authors.lastname: Fisk
authors.forename: Timothy L
authors.initials: TL
authors.lastname: Friebe
authors.forename: Jetze J
authors.initials: JJ
authors.lastname: Tepe
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D004952:Esters; D004987:Ethers / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D010081:Oxazolone / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D000480:Alkynes; D002264:Carboxylic Acids; D004952:Esters; D004987:Ethers; D007659:Ketones; D010081:Oxazolone