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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Enantioselective Assembly of Planar-Chiral and Axial-Planar-Chiral Macrocycles via De Novo Isoquinolinone Formation
Wenkai Li1, Ke Yang1, Xiaoli Gu1
1State Key Laboratory of Fine Chemicals, Department of Pharmaceutical Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. China.
Abstract:
A mild cobalt/salicyloxazoline (Salox)-catalyzed intramolecular C-H macrocyclization is reported. This method enables the enantioselective synthesis of planar-chiral macrocycles as well as scaffolds integrating planar and axial chirality. The reaction proceeds under mild conditions, shows broad substrate scope, and delivers products in yields of 42% to 73% with excellent enantioselectivities (up to 99% ee). This work establishes a versatile platform for constructing constrained, three-dimensional macrocyclic architectures.
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