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- Title
Enantioselective Synthesis of N‐N Atropisomers by Palladium‐Catalyzed C−H Functionalization of Pyrroles.
- Authors
Yao, Wang; Lu, Chuan‐Jun; Zhan, Li‐Wen; Wu, Yi; Feng, Jia; Liu, Ren‐Rong
- 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.
- Subjects
ATROPISOMERS; PYRROLES; KINETIC resolution; FRIEDEL-Crafts reaction; ALKENYLATION; ARYLATION
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 21, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202218871