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Enantioselective Tandem Cyclization of Alkyne‐Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis
Author(s) -
Zhu Yugen,
He Wei,
Wang Wei,
Pitsch Chloe E.,
Wang Xiaotai,
Wang Xiang
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706694
Subject(s) - enantioselective synthesis , alkyne , phosphoric acid , chemistry , catalysis , indole test , combinatorial chemistry , nucleophile , hydrogen bond , transfer hydrogenation , organic chemistry , stereochemistry , molecule , ruthenium
Reported is the enantioselective synthesis of tetracyclic indolines using silver(I)/chiral phosphoric acid catalysis. A variety of alkyne‐tethered indoles are suitable for this process. Mechanistic studies suggest that the in situ generated silver(I) chiral phosphate activates both the alkyne and the indole nucleophile in the initial cyclization step through an intermolecular hydrogen bond and the phosphate anion promotes proton transfer. In addition, further modifications of the cyclization products enabled stereochemistry–function studies of a series of bioactive indolines.