Cobalt-Catalyzed Regio, Diastereo, and Enantioselective C–H Annulation of Aminoquinoline Amides with Internal Alkynes for the Construction of Diaxes
Xi Wu , Qingyu Tian , Jin Ge , Yaopeng Liu , Zhenghao Li , Jie Zhang , Guolin Cheng
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (20) : 2669 -2676.
Cobalt-Catalyzed Regio, Diastereo, and Enantioselective C–H Annulation of Aminoquinoline Amides with Internal Alkynes for the Construction of Diaxes
Transition metal-catalyzed functionalization of unsymmetrical internal alkynes remains challenging because of the difficulty in controlling regioselectivity of migratory insertion of alkynes into the C–metal bonds. Moreover, the synthesis of C–N atropisomers has received significantly less attention compared to that of C–C atropisomers and there have been only a few isolated examples reported for the construction of chiral diaxes through C–H functionalization. Herein, we report that cobalt can catalyze the C–H annulations of aminoquinoline amides with directing group-tethered internal alkynes or 1-indolylalkynes for the synthesis of chiral diaxes. A variety of vicinal C–N and C–C chiral diaxes and distal double C–N chiral diaxes were synthesized with excellent regio, diastereo, and enantioselectivity under mild reaction conditions. The ready availability of aminoquinoline amides, alkynes, and Salox ligands and the simplicity and good functional group tolerance of this protocol make it highly attractive.
Cobalt / Asymmetric catalysis / C–H activation / Internal alkyne / Atropisomerism / Cyclization / N-Heterocycles / Enantioselectivity
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
/
| 〈 |
|
〉 |
PDF
