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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Phosphine-Catalyzed Atroposelective Formal [3 + 2] Cycloaddition Desymmetrization of N-Arylmaleimides
Huamin Wang1, Yibo Wei1, Yuqiang Li2
1School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001, People's Republic of China.
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.
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