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

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 s...

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Bibliographic Details
Published in:Tetrahedron 2017-02, Vol.73 (8), p.1120-1126
Main Authors: Fedotova, Alena I., Komarova, Tatiana A., Romanov, Alexey R., Ushakov, Igor A., Legros, Julien, Maddaluno, Jacques, Rulev, Alexander Yu
Format: Article
Language:English
Subjects:
Aminoadamantane
Aza-Michael addition
Aziridines
Chemical Sciences
Organic chemistry
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.01.006