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Two-Step Synthesis of 2,3-Dihydropyrroles via a Formal 5- endo Cycloisomerization of Ugi 4-CR/Propargyl Adducts

2012; American Chemical Society; Volume: 14; Issue: 21 Linguagem: Inglês

10.1021/ol3024727

1523-7060

Luis A. Polindara‐García, Luis D. Miranda,

Cyclopropane Reaction Mechanisms

A practical two-step synthesis of 2,3-dihydropyrroles from Ugi 4-CR/propargyl adducts is presented. The protocol includes a base-mediated formation of an allenamide functional group and an in situ metal-free formal 5-endo cycloisomerization that occurs in a highly regioselective manner at the allenamide C-γ.