Synthesis of Chiral Piperazinones Using Amphoteric Aziridine Aldehyde Dimers and Functionalized Isocyanides

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• 作者：Niklas B. Heine ; Sherif J. Kaldas ; Lee Belding ; Olga Shmatova ; Travis Dudding ; Valentine G. Nenajdenko ; Armido Studer ; Andrei K. Yudin
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：June 17, 2016
• 年：2016
• 卷：81
• 期：12
• 页码：5209-5216
• 全文大小：327K
• 年卷期：0
• ISSN：1520-6904

文摘

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.