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Gold‐Catalyzed Asymmetric Intramolecular Cyclization of N‐Allenamides for the Synthesis of Chiral Tetrahydrocarbolines
Author(s) -
Wang Yidong,
Zhang Peichao,
Di Xiaoyu,
Dai Qiang,
Zhang ZhanMing,
Zhang Junliang
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709595
Subject(s) - enantioselective synthesis , desymmetrization , intramolecular force , chemistry , catalysis , combinatorial chemistry , phos , stereocenter , ligand (biochemistry) , phosphine , stereochemistry , organic chemistry , receptor , biochemistry
Highly enantioselective gold‐catalyzed intramolecular cyclization of N‐allenamides was implemented by utilizing a designed chiral sulfinamide phosphine ligand (PC‐Phos). This represents the first example of highly enantioselective intramolecular cyclization of N‐allenamides. The practicality of this reaction was validated in the total synthesis of ( R )‐desbromoarborescidine A and formal synthesis of ( R )‐desbromoarborescidine C and ( R )‐deplancheine. Moreover, the catalyst system PC‐Phos/AuNTf 2 proved to be specifically efficient to promote the desymmetrization of N‐allenamides in excellent yields with satisfactory ee values.