Synthesis of Functionalized Tetrahydropyridines by SnCl4‐Mediated Cycloaddition between Donor–AcceptorCyclobutanes and Nitriles

Cycloadditions of strained carbocycles promoted by Lewis acids are powerful methods to construct heterocyclic frameworks. In fact, the formal [3+2] cycloadditions of donor–acceptor (DA) cyclopropanes with nitriles has seen particular success in synthesis. In this work, we report on the first [4+2] c...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry : a European journal 2019-12, Vol.25 (67), p.15244-15247
Hauptverfasser: Tong, David, Wu, Jackie, Bazinski, Nathan, Koo, Donghyun, Vemula, Naresh, Pagenkopf, Brian L
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Cycloadditions of strained carbocycles promoted by Lewis acids are powerful methods to construct heterocyclic frameworks. In fact, the formal [3+2] cycloadditions of donor–acceptor (DA) cyclopropanes with nitriles has seen particular success in synthesis. In this work, we report on the first [4+2] cycloaddition of nitriles with DA cyclobutanes by Lewis acid activation. Tetrahydropyridine derivatives were obtained in up to 91 % yield from various aryl‐activated cyclobutane diesters and aliphatic or aromatic nitriles.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201903833