Versatile "traceless" sulfone linker for SPOS: Preparation of isoxazolinopyrrole 2-carboxylates

Sung Hee Hwang, Mark J. Kurth

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

A five-step solid-phase synthesis of isoxazolinopyrrole-2-carboxylates (6) that employs a traceless sulfone linker strategy is reported. Resin-bound diene 4, obtained by acetylation and concomitant β-elimination of acetate from resin-bound allylic alcohol 3, underwent regioselective 1,3-dipolar cycloadditons with nitrile oxides. Formation of the pyrrole products in a resin-releasing strategy was performed by pyrrole annulation with alkyl isocyanoacetates, which react with the vinyl sulfone moiety to generate the target isoxazolinopyrrole-2-carboxylates (6). Use of this chemistry afforded eight isoxazolinopyrrole-2-carboxylates in 6-24% overall yields from polystyrene/divinylbenzene sulfinate 1.

Original languageEnglish (US)
Pages (from-to)6564-6567
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number18
DOIs
StatePublished - Sep 6 2002

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Sulfones
Pyrroles
divinyl benzene
Resins
Acetylation
Nitriles
Polystyrenes
Oxides
Acetates

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Versatile "traceless" sulfone linker for SPOS : Preparation of isoxazolinopyrrole 2-carboxylates. / Hwang, Sung Hee; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 67, No. 18, 06.09.2002, p. 6564-6567.

Research output: Contribution to journalArticle

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