Chiral phosphoric acid-catalyzed asymmetric epoxidation of alkenyl aza-heteroarenes using hydrogen peroxide

Hao-Chen Wen, Wei Chen, Meng Li, Chen Ma, Jian-Fei Wang, Aiping Fu, Shi-Qi Xu, Yi-Feng Zhou, Shao-Fei Ni () and Bin Mao ()
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Hao-Chen Wen: Zhejiang University of Technology
Wei Chen: Zhejiang University of Technology
Meng Li: Zhejiang University of Technology
Chen Ma: Shantou University
Jian-Fei Wang: Zhejiang University of Technology
Aiping Fu: Zhejiang University of Technology
Shi-Qi Xu: Zhejiang University of Technology
Yi-Feng Zhou: China Jiliang University
Shao-Fei Ni: Shantou University
Bin Mao: Zhejiang University of Technology

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract The synthesis of chiral α-azaheteroaryl oxiranes via enantioselective catalysis is a formidable challenge due to the required complex stereoselectivity and diverse N-heterocyclic structures. These compounds play a crucial role in developing bioactive molecules, where precise chirality significantly influences biological activity. Here we show that using chiral phosphoric acid as a catalyst, our method efficiently addresses these challenges. This technique not only achieves high enantio- and diastereoselectivity but also demonstrates superior chemo- and stereocontrol during the epoxidation of alkenyl aza-heteroarenes. Our approach leverages a synergistic blend of electrostatic and hydrogen-bonding interactions, enabling the effective activation of both substrates and hydrogen peroxide. The resulting chiral oxiranes exhibit enhanced diversity and functionality, aiding the construction of complex chiral azaaryl compounds with contiguous stereocenters. Kinetic and density functional theory studies elucidate the mechanism, highlighting chiral phosphoric acid’s pivotal role in this intricate enantioselective process.

Date: 2024
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DOI: 10.1038/s41467-024-49435-2

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