ArticleNature communications2025
Concise synthesis of chiral tricyclic γ-lactams via synergistic isothiourea/Ir catalyzed asymmetric [3 + 2] annulation.
Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Accessing trans-fused N-fused tricyclic frameworks with multiple contiguous stereocenters remains a major challenge in synthesis. We report a synergistic isothiourea/Ir-catalyzed [3 + 2] annulation of arylacetic acid esters with azabenzonorbornadienes, providing trans-fused tricyclic γ-lactams with three contiguous tertiary stereocenters in high regio-, enantio-, and diastereoselectivity. The method tolerates diverse arylacetates, heterocycles, and pharmaceutically relevant carboxylates, and is amenable to gram-scale synthesis. Mechanistic studies support a cooperative cycle involving C1-ammonium enolate formation and enantioselective S
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