Enantioselective Synthesis of Azahelicenes via Rh-Catalyzed C–H Functionalization of 6-Hydroxyisoquinoline Derivatives with Alkynes
Abstract
Abstract Herein, we report an asymmetric C–H functionalization of 6-hydroxyisoquinoline derivatives and annulation with internal alkynes. The reaction is catalyzed by a chiral cyclopentadienyl (Cp)-Rh complex in combination with a modified chiral amino acid. A series of azahelicenes is afforded in good yields (up to 93%) with high enantioselectivity (up to 99% ee). A plausible catalytic cycle is proposed based on control experiments and DFT calculations, involving the reductive elimination from a high-valent Rh intermediate.
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Authors: Wei Zhang, Pei‐Pei Xie, Qiang Wang, Wang Rui-Xiang, Yi-Liang Gong, Yanze Li, Chao Zheng, Shu‐Li You
Institutions: Second Military Medical University, Central China Normal University, Shanghai Institute of Organic Chemistry