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 Citations (Scopus)

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

Fingerprint

Solid-Phase Synthesis Techniques
Sulfones
sulfones
solid phases
alkylation
Alkylation
synthesis
Nitriles
Cycloaddition
nitriles
Cycloaddition Reaction
cycloaddition
Oxides
cleavage
elimination
Derivatives
Oxidation
preparation
oxidation
oxides

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.

Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones. / Cheng, Wei Chieh; Wong, Melissa; Olmstead, Marilyn M.; Kurth, Mark J.

In: Organic Letters, Vol. 4, No. 5, 07.03.2002, p. 741-744.

Research output: Contribution to journalArticle

Cheng, WC, Wong, M, Olmstead, MM & Kurth, MJ 2002, 'Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones', Organic Letters, vol. 4, no. 5, pp. 741-744.
Cheng WC, Wong M, Olmstead MM, Kurth MJ. Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones. Organic Letters. 2002 Mar 7;4(5):741-744.
Cheng, Wei Chieh ; Wong, Melissa ; Olmstead, Marilyn M. ; Kurth, Mark J. / Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones. In: Organic Letters. 2002 ; Vol. 4, No. 5. pp. 741-744.
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