Phosphine-Catalyzed Atroposelective Formal [3 + 2] Cycloaddition Desymmetrization of <i>N</i>-Arylmaleimides
Huamin Wang, Yibo Wei, Yuqiang Li, Shuangshuang Long, Li-Juan Sun, Shixiong Li, Ying‐Wu Lin
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.
Topics & Concepts
SuccinimidesDesymmetrizationChemistryStereocenterAnnulationEnantioselective synthesisArylAxial chiralityPhosphineAtropisomerCatalysisCombinatorial chemistryCycloadditionStereochemistryOrganic chemistryAlkylAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis