使用两性氮杂环丙烷醛二聚体和功能化异氰化物合成手性哌嗪酮。
Synthesis of Chiral Piperazinones Using Amphoteric Aziridine Aldehyde Dimers and Functionalized Isocyanides.
机构信息
Organic Chemistry Institute, Westfälische Wilhelms-Universität , Corrensstraße 40, 48149 Münster, Germany.
Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario M5S 3H6 Canada.
出版信息
J Org Chem. 2016 Jun 17;81(12):5209-16. doi: 10.1021/acs.joc.6b00471. Epub 2016 Jun 1.
We have evaluated a range of functionalized isocyanides in the aziridine aldehyde-driven multicomponent synthesis of piperazinones. High diasteroselectivity for each isocyanide was observed. A theoretical evaluation of the reaction course corroborates the experimental data. Moreover, the reactivity of cis- and trans-configured aziridine aldehyde dimers has been compared. This study further probes the dimer-driven mechanism of cyclization and enables an efficient access to a wide range of chiral piperazinones bearing functionalized side chains.
我们在氮丙啶醛驱动的多组分合成哌嗪酮中评估了一系列功能化异氰化物。观察到每种异氰化物具有很高的非对映选择性。反应过程的理论评估证实了实验数据。此外，还比较了顺式和反式构型氮丙啶醛二聚体的反应性。这项研究进一步探究了二聚体驱动的环化机制，并能够有效地获得具有功能化侧链的广泛的手性哌嗪酮。
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