Copper(II) Trifluoromethanesulfonate Catalyzed Hydroamination Cyclization–Dimerization Cascade Reaction of Homopropargylic Amines for the Construction of Complex Fused Nitrogen‐Containing Tetracycles. Issue 22 (13th July 2016)

• Record Type: Journal Article
• Authors: Liu, Lingyan; Wang, Chan; Liu, Qiangqiang; Kong, Yuanfang; Chang, Weixing; Li, Jing
• Is Part Of: European journal of organic chemistry. Issue 22(2016)
• Page Start: 3684
• Page End: 3690
• Publication Date: 2016-07-13
• Subjects: Homogeneous catalysis -- Domino reactions -- Hydroamination -- Cyclization -- Alkaloids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600692
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : 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.