Solid-phase synthesis of isoxazoles using vinyl ethers as chameleon catches.
[reaction: see text] Regioselective 1,3-dipolar cycloadditions of supported vinyl ethers R(1)C(=CH(2))O-CH(2)-polymer, prepared by the Tebbe olefination of R(1)CO(2)-CH(2)-polymer, with ethyl cyanoformate N-oxide gave supported isoxazoline derivatives. Release from the support under mild acidic conditions gave the isoxazoles ethyl 5-R(1)-isoxazole-3-carboxylates. Alternatively, further on-resin functionalization of the R(1) substituent using Suzuki coupling reactions and release from the support under acidic conditions gave more structurally diverse isoxazoles.
Barrett
A G
AG
Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, UK. agmb@ic.ac.uk
Procopiou
P A
PA
Voigtmann
U
U
D004987:Ethers / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D004987:Ethers; D007555:Isoxazoles; D014753:Vinyl Compounds