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- Title
Chiral phosphoric acid-catalyzed asymmetric epoxidation of alkenyl aza-heteroarenes using hydrogen peroxide.
- Authors
Wen, Hao-Chen; Chen, Wei; Li, Meng; Ma, Chen; Wang, Jian-Fei; Fu, Aiping; Xu, Shi-Qi; Zhou, Yi-Feng; Ni, Shao-Fei; Mao, Bin
- 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. Chiral azaarenes hold critical importance in pharmaceutical research due to their significant impact on drug efficacy and selectivity. Herein, the authors report the synthesis of chiral α-azaheteroaryl oxiranes via catalytic enantioselective epoxidation of alkenyl aza-heteroarenes using chiral phosphoric acid and hydrogen peroxide.
- Subjects
HYDROGEN peroxide; PHOSPHORIC acid; EPOXIDATION; ENANTIOSELECTIVE catalysis; ALKENYL group; DENSITY functional theory; ACID catalysts
- Publication
Nature Communications, 2024, Vol 15, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-024-49435-2