Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones

Wei Chieh Cheng, Melissa Wong, Marilyn M. Olmstead, Mark J. Kurth

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

(equation presented) 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 → 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 → cyclobutanone oxidation with concomitant linker cleavage by sulfinate elimination.

Original languageEnglish (US)
Pages (from-to)741-744
Number of pages4
JournalOrganic Letters
Volume4
Issue number5
StatePublished - Mar 7 2002

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ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Cheng, W. C., Wong, M., Olmstead, M. M., & Kurth, M. J. (2002). Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones. Organic Letters, 4(5), 741-744.