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 |
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ASJC Scopus subject areas
- Organic Chemistry
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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 journal › Article
}
TY - JOUR
T1 - Versatile "traceless" sulfone linker for SPOS
T2 - Preparation of isoxazolinopyrrole 2-carboxylates
AU - Hwang, Sung Hee
AU - Kurth, Mark J.
PY - 2002/9/6
Y1 - 2002/9/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0037031635&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037031635&partnerID=8YFLogxK
U2 - 10.1021/jo016377k
DO - 10.1021/jo016377k
M3 - Article
C2 - 12201785
AN - SCOPUS:0037031635
VL - 67
SP - 6564
EP - 6567
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 18
ER -