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- Title
Enantioselective Synthesis of Benzimidazole Atropisomers Featuring a N-N Axis.
- Authors
Fang-Bei Ge; Qi-Kun Yin; Chuan-Jun Lu; Xuan Xuan; Jia Feng; Ren-Rong Liu
- Abstract
Atroposelective synthesis of N-N atropisomers is an emerging area but remains underexplored; in particular, the synthesis of N-N benzimidazole atropisomers is still unprecedented. Herein, the first enantioselective synthesis of N-N benzimidazole atropisomers via the palladium-catalyzed de novo construction of benzimidazole skeleton is presented. With readily available palladium catalyst and biphosphine ligand, a broad range of nonbiaryl benzimidazole and indole-benzimidazole atropisomers were conveniently accessed in high yields and with excellent enantioselectivities. Significantly, these N-N benzimidazole atropisomers showed great antitumor activity and selectivity to breast cancer MCF-7 cells. The simple catalytic system, broad substrate scope, high enantioselectivity, and good bioactivity make this approach highly attractive.
- Subjects
ATROPISOMERS; PALLADIUM catalysts; BREAST cancer; ANTINEOPLASTIC agents; CANCER cells
- Publication
Chinese Journal of Chemistry, 2024, Vol 42, Issue 7, p711
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.202300600