Versatile "traceless" sulfone linker for SPOS: preparation of isoxazolinopyrrole 2-carboxylates |
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Authors: | Hwang Sung Hee Kurth Mark J |
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Institution: | Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616-5295, USA. |
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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 beta-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. |
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