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Copper(II) Trifluoromethanesulfonate Catalyzed Hydroamination Cyclization–Dimerization Cascade Reaction of Homopropargylic Amines for the Construction of Complex Fused Nitrogen‐Containing Tetracycles
Author(s) -
Liu Lingyan,
Wang Chan,
Liu Qiangqiang,
Kong Yuanfang,
Chang Weixing,
Li Jing
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600692
Subject(s) - chemistry , hydroamination , stereocenter , trifluoromethanesulfonate , cascade reaction , catalysis , radical cyclization , cascade , intramolecular force , natural product , combinatorial chemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , chromatography
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.