Enantioselective Copper-Catalyzed Alkylation of Quinoline N-Oxides with Vinylarenes

Songjie Yu, Hui Leng Sang, Shaozhong Ge*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

41 Citations (Scopus)

Abstract

An asymmetric copper-catalyzed alkylation of quinoline N-oxides with chiral Cu–alkyl species, generated by migratory insertion of a vinylarene into a chiral Cu−H complex, is reported. A variety of quinoline N-oxides and vinylarenes underwent this Cu-catalyzed enantioselective alkylation reaction, affording the corresponding chiral alkylated N-heteroarenes in high yield with high-to-excellent enantioselectivity. This enantioselective protocol represents the first general and practical approach to access a wide range of chiral alkylated quinolines.

Original languageEnglish
Pages (from-to)15896-15900
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number50
Early online date16 Oct 2017
DOIs
Publication statusPublished - 11 Dec 2017

Keywords

  • alkylation
  • asymmetric catalysis
  • copper
  • quinoline N-oxides
  • vinylarenes

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