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

Yugen Zhu, Wei He, Wei Wang, Chloe E. Pitsch, Xiaotai Wang*, Xiang Wang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)12206-12209
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number40
DOIs
Publication statusPublished - 25 Sept 2017
Externally publishedYes

Keywords

  • asymmetric catalysis
  • cyclization
  • density functional calculations
  • polycycles
  • silver

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