1. Enantioselective Synthesis of N‐N Atropisomers by Palladium‐Catalyzed C−H Functionalization of Pyrroles.
- Author
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Yao, Wang, Lu, Chuan‐Jun, Zhan, Li‐Wen, Wu, Yi, Feng, Jia, and Liu, Ren‐Rong
- Subjects
ATROPISOMERS ,PYRROLES ,KINETIC resolution ,FRIEDEL-Crafts reaction ,ALKENYLATION ,ARYLATION - Abstract
The catalytic asymmetric construction of N−N atropisomeric biaryls remains a formidable challenge. Studies of them lag far behind studies of the more classical carbon‐carbon biaryl atropisomers, hampering meaningful development. Herein, the first palladium‐catalyzed enantioselective C−H activation of pyrroles for the synthesis of N−N atropisomers is presented. Structurally diverse indole‐pyrrole atropisomers possessing a chiral N−N axis were produced with good yields and high enantioselectivities by alkenylation, alkynylation, allylation, or arylation reactions. Furthermore, the kinetic resolution of trisubstituted N−N heterobiaryls with more sterically demanding substituents was also achieved. Importantly, this versatile C−H functionalization strategy enables iterative functionalization of pyrroles with exquisite selectivity, expediting the formation of valuable, complex, N−N atropisomers. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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