A copper(II)-catalyzed, sequential Michael-aldol reaction for the preparation of 1,2-dihydroquinolines

Anna M. Wagner, Claire E. Knezevic, Jessica L. Wall, Victoria L. Sun, Joshua A. Buss, Leeann T. Allen, Anna G. Wenzel

Research output: Contribution to journalArticlepeer-review

Abstract

A copper(II)-catalyzed, sequential Michael addition-aldol condensation reaction of N-carboxybenzyl-protected aminobenzaldehyde with various α,β-unsaturated N-acyl pyrroles is described. Substrate scope was found to include both aryl and aliphatic N-acyl pyrroles as the Michael acceptors, and isolated product yields as high as 93% were observed. The use of acetonitrile as the reaction solvent proved to be crucial for catalysis, both to function as a labile ligand for copper, as well as an agent to minimize hydrolytic catalyst poisoning.

Original languageEnglish (US)
Pages (from-to)833-836
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number7
DOIs
StatePublished - Feb 15 2012
Externally publishedYes

Keywords

  • Acetonitrile
  • Heterocycles
  • Lewis acid catalysis
  • Michael-aldol reaction
  • Small-molecule synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'A copper(II)-catalyzed, sequential Michael-aldol reaction for the preparation of 1,2-dihydroquinolines'. Together they form a unique fingerprint.

Cite this