ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2025
Asymmetric [3 + 2] Cycloaddition to Access 3-Pyrrolines and Their Switchable Transformations to Nine-Membered Cyclic Sulfamidates and 2H-Pyrroles.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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Who cites it
1 citing paper in PubMed.
- Asymmetric [3 + 2] Cycloaddition to Access 3-Pyrrolines and Their Switchable Transformations to Nine-Membered Cyclic Sulfamidates and 2H-Pyrroles.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
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3 authors.
Funding
Abstract
Herein, Pd-catalyzed asymmetric [3 + 2] cycloaddition and olefin isomerization is reported to afford chiral 3-pyrrolines using cyano-TMM (trimethylenemethane) and cyclic sulfamidate imines. This represents a unique protocol to provide chiral N-heterocycles bearing endocyclic olefins by asymmetric Pd-TMM cycloaddition. The developed Pd-catalyzed cycloaddition further extends to versatile synthetic transformations, offering a facile and unified approach to synthetically challenging yet valuable classes of heterocycles, including medium-sized sulfamidate rings and 2H-pyrroles, in a one-pot operation. In particular, chemo-switchable ring expansion and desulfonylation of sulfamidate-fused 3-pyrrolines are achieved by simple solvent and temperature changes under identical alkoxide base conditions.
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