General and efficient organocatalytic synthesis of indoloquinolizidines, pyridoquinazolines and quinazolinones through a one-pot domino michael addition-cyclization-pictet-spengler or 1,2-amine addition reaction

Magnus Rueping*, Chandra M.R. Volla, Michael Bolte, Gerhard Raabe

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

An asymmetric organocatalyzed reaction sequence involving a Michael addition of various 1,3-dicarbonyl compounds to α,β-unsaturated aldehydes with subsequent diastereoselective Pictet-Spengler cyclization has been developed. The substrate scope was found to be general and optically active indoloquinolizidines were isolated as single diastereomers in high yields with high to excellent enantioselectivites. In addition to tryptamine, the reaction has also been successfully applied to other nucleophiles including o-aminobenzylamine and anthranilamide giving rise to pyridoquinauolines and quinazolinones.

Original languageEnglish (US)
Pages (from-to)2853-2859
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number14-15
DOIs
StatePublished - Oct 1 2011

Keywords

  • Brønsted acids
  • Lewis base catalyis
  • Mannich reaction
  • diarylprolinol ethers
  • multicomponent reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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