Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones.
[reaction: see text] The preparation of novel isoxazolocyclobutanone and isoxazolinocyclobutenone derivatives via a traceless solid-phase sulfone linker strategy is described. Key steps in the solid-phase protocol reported here include (i) sulfinate right arrow sulfone alkylation, (ii) four-member ring formation by sulfone dianion alkylation, (iii) heterocycle formation by nitrile oxide 1,3-dipolar cycloaddition, and (iv) traceless product release by cyclobutanol right arrow cyclobutanone oxidation with concomitant linker cleavage by sulfinate elimination.
Cheng
Wei-Chieh
WC
Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616-5295, USA.
Wong
Melissa
M
Olmstead
Marilyn M
MM
Kurth
Mark J
MJ