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- Title
Atropisomeric Carboxylic Acids Synthesis via Nickel‐Catalyzed Enantioconvergent Carboxylation of Aza‐Biaryl Triflates with CO<sub>2</sub>.
- Authors
Chen, Xiao‐Wang; Li, Chao; Gui, Yong‐Yuan; Yue, Jun‐Ping; Zhou, Qi; Liao, Li‐Li; Yang, Jing‐Wei; Ye, Jian‐Heng; Yu, Da‐Gang
- Abstract
Upgrading CO2 to value‐added chiral molecules via catalytic asymmetric C−C bond formation is a highly important yet challenging task. Although great progress on the formation of centrally chiral carboxylic acids has been achieved, catalytic construction of axially chiral carboxylic acids with CO2 has never been reported to date. Herein, we report the first catalytic asymmetric synthesis of axially chiral carboxylic acids with CO2, which is enabled by nickel‐catalyzed dynamic kinetic asymmetric reductive carboxylation of racemic aza‐biaryl triflates. A variety of important axially chiral carboxylic acids, which are valuable but difficult to obtain via catalysis, are generated in an enantioconvergent version. This new methodology features good functional group tolerance, easy to scale‐up, facile transformation and avoids cumbersome steps, handling organometallic reagents and using stoichiometric chiral materials. Mechanistic investigations indicate a dynamic kinetic asymmetric transformation process induced by chiral nickel catalysis.
- Subjects
CARBOXYLIC acids; CARBOXYLATION; DERACEMIZATION; ENANTIOSELECTIVE catalysis; ASYMMETRIC synthesis; CHIRALITY element; FUNCTIONAL groups
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 22, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202403401