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Access to distal biaxial atropisomers by iridium catalyzed asymmetric C-H alkylation.

ABSTRACT: Distal biaxial atropisomers are typical structures in chiral catalysts and ligands and offer a wide variety of applications in biology and materials technology, but the development of efficient synthesis of these valuable scaffolds is still in great demand. Herein, we describe a highly efficient iridium catalyzed asymmetric C-H alkylation reaction that provides a range of new distal biaxial atropisomers with excellent yields (up to 99%) and stereoselectivity (up to 99% ee and essentially one isomer). Based on this unprecedented strategy, a polycyclic skeleton with five successive chiral centers as well as C-C and C-N (or N-N) two distal chiral axes was created successfully in mild circumstances. In addition, the optically pure products bearing fluorophores show circular polarized luminescence (CPL) properties, being potential candidate materials for CPL applications.

SUBMITTER: Hu X

PROVIDER: S-EPMC11339954 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Access to distal biaxial atropisomers by iridium catalyzed asymmetric C-H alkylation.

Hu Xueqing X Zhao Yunxu Y He Tong T Niu Caoyue C Liu Feipeng F Jia Wei W Mu Yi Y Li Xingwei X Rong Zi-Qiang ZQ

Chemical science 20240722 33

Distal biaxial atropisomers are typical structures in chiral catalysts and ligands and offer a wide variety of applications in biology and materials technology, but the development of efficient synthesis of these valuable scaffolds is still in great demand. Herein, we describe a highly efficient iridium catalyzed asymmetric C-H alkylation reaction that provides a range of new distal biaxial atropisomers with excellent yields (up to 99%) and stereoselectivity (up to 99% ee and essentially one iso ...[more]

PMID: 39183921

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