硝基苯
Pauson–Khand反应
类型(生物学)
化学
立体化学
有机化学
生物
生态学
催化作用
分子内力
作者
Fang Li,Wenyong Zhu,Claire Empel,Oleksandr Datsenko,Adarsh Kumar,Y.D. Xu,Johanna H. M. Ehrler,Iuliana Atodiresei,Stefan Knapp,Pavel K. Mykhailiuk,Ewgenij Proschak,René M. Koenigs
出处
期刊:Science
[American Association for the Advancement of Science (AAAS)]
日期:2024-02-02
卷期号:383 (6682): 498-503
标识
DOI:10.1126/science.adm8095
摘要
The Pauson-Khand reaction has in the past 50 years become one of the most common cycloaddition reactions in chemistry. Coupling two unsaturated bonds with carbon monoxide, the transformation remains limited to CO as a C 1 building block. Herein we report analogous cycloaddition reactions with nitrenes as an N 1 unit. The reaction of a nonconjugated diene with a nitrene precursor produces bicyclic bioisosteres of common saturated heterocycles such as piperidine, morpholine, and piperazine. Experimental and computational mechanistic studies support relaying of the diradical nature of triplet nitrene into the π-system. We showcase the reaction’s utility in late-stage functionalization of drug compounds and discovery of soluble epoxide hydrolase inhibitors.
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