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 language | English (US) |
|---|---|
| Pages (from-to) | 6564-6567 |
| Number of pages | 4 |
| Journal | Journal of Organic Chemistry |
| Volume | 67 |
| Issue number | 18 |
| DOIs | |
| State | Published - Sep 6 2002 |
ASJC Scopus subject areas
- Organic Chemistry
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Hwang, S. H., & Kurth, M. J. (2002). Versatile "traceless" sulfone linker for SPOS: Preparation of isoxazolinopyrrole 2-carboxylates. Journal of Organic Chemistry, 67(18), 6564-6567. https://doi.org/10.1021/jo016377k