Synthesis of tert-alkyl amino hydroxy carboxylic esters via an intermolecular ene-type reaction of oxazolones and enol ethers.
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.
Mosey
Robert A
RA
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Fisk
Jason S
JS
Friebe
Timothy L
TL
Tepe
Jetze J
JJ
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*
D000480:Alkynes; D002264:Carboxylic Acids; D004952:Esters; D004987:Ethers; D007659:Ketones; D010081:Oxazolone