Rhodium(III)-Catalyzed Enantioselective C–H Activation/Annulation of Ferrocenecarboxamides with Internal Alkynes
journal contributionposted on 2022-02-21, 15:08 authored by Quannan Wang, Yu-Han Nie, Chen-Xu Liu, Wen-Wen Zhang, Zhi-Jie Wu, Qing Gu, Chao Zheng, Shu-Li You
Efficient synthesis of planar chiral ferrocene-fused heterocyclic molecules is challenging in asymmetric synthesis. Herein, we report an enantioselective C–H activation/annulation of ferrocenecarboxamides with internal alkynes promoted by CpRh(III) catalysis. Trisubstituted chiral Cp-derived Rh complexes are found to be enabling catalysts, which lead to a broad substrate scope with good functional group compatibility. Planar chiral ferrocene-fused pyridone products are obtained in high yields (up to 90%) with excellent enantioselectivity (up to 99% ee). Combined experimental and computational studies support the proposed reaction mechanism.
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trisubstituted chiral cpproposed reaction mechanismplanar chiral ferroceneinternal alkynes promotedfused pyridone productsfused heterocyclic moleculesderived rh complexescprh ( iiicomputational studies supportbroad substrate scopehigh yieldsexcellent enantioselectivityenabling catalystsee ).combined experimentalasymmetric synthesis90 %)