A combined continuous microflow photochemistry and asymmetric organocatalysis approach for the enantioselective synthesis of tetrahydroquinolines

Erli Sugiono*, Magnus Rueping

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

A continuous-flow asymmetric organocatalytic photocyclization-transfer hydrogenation cascade reaction has been developed. The new protocol allows the synthesis of tetrahydroquinolines from readily available 2-aminochalcones using a combination of photochemistry and asymmetric Brønsted acid catalysis. The photocylization and subsequent reduction was performed with catalytic amount of chiral BINOL derived phosphoric acid diester and Hantzsch dihydropyridine as hydrogen source providing the desired products in good yields and with excellent enantioselectivities.

Original languageEnglish (US)
Pages (from-to)2457-2462
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
StatePublished - Nov 13 2013

Keywords

  • Asymmetric transfer hydrogenation
  • Binolphosphate
  • Continuous-flow reactors
  • Flow chemistry
  • Microreactors
  • Organocatalysis
  • Photochemistry

ASJC Scopus subject areas

  • Organic Chemistry

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