American Chemical Society
jo7b02193_si_001.pdf (2.92 MB)

Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids

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journal contribution
posted on 2017-10-19, 00:00 authored by Evgeny M. Buev, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh
Active methylene compounds react with in situ generated nonstabilized azomethine ylides via the domino Mannich reaction–dipolar cycloaddition to form 3,3-disubstituted pyrrolidines, including oxindole alkaloids. When the starting material possesses a single activated hydrogen, the reaction terminates at the Mannich base stage. The developed methodology was applied to a short and efficient synthesis of (±)-horsfiline and N-protected (±)-coerulescine.