Copper(II) Trifluoromethanesulfonate Catalyzed Hydroamination Cyclization-Dimerization Cascade Reaction of Homopropargylic Amines for the Construction of Complex Fused Nitrogen-Containing Tetracycles

A Cu(OTf)2‐catalyzed cascade cyclization reaction of simple homopropargylic amines was developed. The sequence involved an intramolecular radical hydroamination cyclization followed by dimerization by a Povarov‐type reaction. Through this cascade reaction, a complex nitrogen‐containing tetracycle fr...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-08, Vol.2016 (22), p.3684-3690
Main Authors: Liu, Lingyan, Wang, Chan, Liu, Qiangqiang, Kong, Yuanfang, Chang, Weixing, Li, Jing
Format: Article
Language:English
Subjects:
Alkaloids
Cyclization
Domino reactions
Homogeneous catalysis
Hydroamination
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Summary:A Cu(OTf)2‐catalyzed cascade cyclization reaction of simple homopropargylic amines was developed. The sequence involved an intramolecular radical hydroamination cyclization followed by dimerization by a Povarov‐type reaction. Through this cascade reaction, a complex nitrogen‐containing tetracycle framework was constructed in one pot with the formation of four new bonds and five stereocenters. Noteworthy, the aglycon of the natural product incargranine B was facilely and efficiently synthesized by using this method. A Cu(OTf)2‐catalyzed intramolecular radical hydroamination cyclization–dimerization cascade reaction of simple homopropargylic amines is developed, and a complex nitrogen‐containing tetracyclic framework is constructed in one pot with the formation of four new bonds and five stereocenters. Noteworthy, the aglycon of the natural product incargranine B is facilely and efficiently synthesized.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600692