A highly enantioselective Brønsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids

Magnus Rueping*, Andrey P. Antonchick, Thomas Theissmann

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

588 Scopus citations

Abstract

(Chemical Equation Presented) A categorical success: A Brønsted acid catalyzed cascade transfer hydrogenation provides direct access to 2-aryl- and 2-alkyl-substituted tetrahydroquinolines with excellent enantioselectivities under mild conditions and using very low amounts of catalyst (see scheme). The best results were achieved with the binol phosphate catalyst, where Ar = 9-phenanthryl, used successfully in the Strecker reaction.

Original languageEnglish (US)
Pages (from-to)3683-3686
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number22
DOIs
StatePublished - May 26 2006

Keywords

  • Asymmetric hydrogenation
  • Brønsted acid
  • Hantzsch dihydropyridine
  • Organocatalysis
  • Tetrahydroquinoline

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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