Adamantyl aziridines via aza-Michael initiated ring closure (aza-MIRC) reaction

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• 作者：Alena I. Fedotova^a ; ^b ; Tatiana A. Komarova^a ; Alexey R. Romanov^a ; Igor A. Ushakov^c ; Julien Legros^b ; ^{julien.legros@univ-rouen.fr} ; Jacques Maddaluno^b ; ^{jmaddalu@crihan.fr} ; Alexander Yu. Rulev^a ; ^{rulev@irioch.irk.ru}
• 关键词：Aza-Michael addition ; Aziridines ; Aminoadamantane
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：23 February 2017
• 年：2017
• 卷：73
• 期：8
• 页码：1120-1126
• 全文大小：502 K
• 卷排序：73

文摘

An efficient one-pot synthesis of functionalized adamantylaziridines by aza-Michael initiated ring closure (aza-MIRC) reaction of 1-aminoadamantane with α-halogenated Michael acceptors is described. The reaction goes through an aza-Michael intermediate that undergoes an intramolecular nucleophilic substitution. Expectedly, high pressure exerts a beneficial influence in the case of sterically hindered reagents.