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Phosphine-Catalyzed Atroposelective Formal [3 + 2] Cycloaddition Desymmetrization of N-Arylmaleimides.

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Herein, a new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was devised by [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This… Click to show full abstract

Herein, a new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was devised by [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This desymmetrization process allows for quick construction of both two stereogenic carbon centers and a remote CAr-N atropisomeric chirality. A series of structurally diverse N-aryl succinimides were obtained with good to excellent yields, diastereoselectivities, and enantioselectivities. The process is mild, efficient, and scalable and features a broad substrate scope.

Keywords: phosphine catalyzed; cycloaddition desymmetrization; atroposelective formal; formal cycloaddition; desymmetrization; catalyzed atroposelective

Journal Title: Organic letters
Year Published: 2022

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