对映选择合成
立体中心
过氧化氢
磷酸
催化作用
手性(物理)
组合化学
化学
立体异构
分子
有机化学
手征对称破缺
夸克
Nambu–Jona Lasinio模型
量子力学
物理
作者
Wen Hong-gen,Wei Chen,Meng Li,Chen Ma,Jianfei Wang,Aiping Fu,Shiqi Xu,Yifeng Zhou,Shao‐Fei Ni,Bin Mao
标识
DOI:10.1038/s41467-024-49435-2
摘要
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.
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