One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles.
[reaction: see text] 3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used in stoichiometric amounts, formation of byproducts is minimized.
Hansen
Trond V
TV
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Wu
Peng
P
Fokin
Valery V
VV
D002384:Catalysis; D003300:Copper / Q000494:pharmacology*; D007555:Isoxazoles / Q000138:chemical synthesis*
D007555:Isoxazoles; D003300:Copper