Enantioselective Tandem Cyclization of Alkyne‐Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis | Zendy

Zhu Yugen | Zendy; He Wei | Zendy; Wang Wei | Zendy; Pitsch Chloe E. | Zendy; Wang Xiaotai | Zendy; Wang Xiang | Zendy

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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) - alkyne , enantioselective synthesis , phosphoric acid , chemistry , catalysis , indole test , combinatorial chemistry , nucleophile , transfer hydrogenation , organic chemistry , hydrogen bond , 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.

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