Asymmetric counterion pair catalysis: An enantioselective Brønsted acid-catalyzed protonation

Magnus Rueping*, Thomas Theissmann, Sadiya Raja, Jan W. Bats

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

158 Scopus citations

Abstract

A new asymmetric Brønsted acid-catalyzed cascade reaction involving a 1,4-addition, enantioselective protonation and 1,2-addition has been developed. This organocatalytic cascade not only provides for the first time 3-and 2,3-substituted tetrahydroquinolines and octahydroacridines in good yields with high dia- and enantioselectivities under mild reaction conditions but additionally represents the first example of a chiral Brønsted acid-catalyzed protonation reaction in an organocatalytic domino reaction. Furthermore, the new Brønsted acid-catalyzed hydride-proton-hydride transfer cascade can be applied to prepare new molecular scaffolds with up to three new stereocenters in an efficient one-pot reaction sequence.

Original languageEnglish (US)
Pages (from-to)1001-1006
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume350
Issue number7-8
DOIs
StatePublished - May 5 2008

Keywords

  • BINOL phosphate
  • Enantioselective isomerization
  • Hantzsch dihydropyridine
  • Organocatalytic cascade reaction
  • Transfer hydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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