钯催化的对甲苯磺酰基乙烯基氮杂环丙烷的羰基化[5+1]环加成反应：溶剂控制的α,β-和β,γ-不饱和δ-内酰胺的发散合成
Palladium-Catalyzed Carbonylative [5+1] Cycloaddition of -Tosyl Vinylaziridines: Solvent-Controlled Divergent Synthesis of α,β- and β,γ-Unsaturated δ-Lactams.
作者信息
Zhang Tao, Wang Shichong, Zuo Dandan, Zhao Jingjing, Luo Wen, Wang Chaojie, Li Pan
机构信息
College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China.
Key Laboratory of Natural Medicine and Immuno-Engineering, Henan University, Kaifeng 475004, P. R. China.
出版信息
J Org Chem. 2022 Aug 5;87(15):10408-10415. doi: 10.1021/acs.joc.2c00710. Epub 2022 Jul 26.
A palladium-catalyzed carbonylative [5+1] cycloaddition of -tosyl vinylaziridines with CO has been developed. This protocol affords an efficient and practical approach for solvent-controlled divergent synthesis of α,β-unsaturated δ-lactams in dimethylformamide and β,γ-unsaturated δ-lactams in tetrahydrofuran in good to excellent yields. Significantly, the step- and atom-economical reactions are more regioselective toward [5+1] cycloaddition than toward [3+1] cycloaddition.
已开发出一种钯催化的对甲苯磺酰基乙烯基氮丙啶与一氧化碳的羰基化[5+1]环加成反应。该方法提供了一种高效实用的方法，可在二甲基甲酰胺中溶剂控制地发散合成α,β-不饱和δ-内酰胺，在四氢呋喃中合成β,γ-不饱和δ-内酰胺，产率良好至优异。值得注意的是，该分步和原子经济反应对[5+1]环加成的区域选择性比对[3+1]环加成的区域选择性更高。
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