Exploration of forbidden Povarov processes as a source of unexpected reactivity: a multicomponent Mannich-Ritter transformation

Angew Chem Int Ed Engl. 2012 Jul 9;51(28):6874-7. doi: 10.1002/anie.201202927. Epub 2012 May 31.

Abstract

When a door closes, a window opens! The use of geometrically or electronically restricted imines for Povarov-type processes does not afford the anti-Bredt tetrahydroquinolines, but leads instead to highly functionalized structures through novel reaction pathways (see picture; LA=Lewis acid). The exploration of "forbidden" routes constitutes a valuable approach in the search for new multicomponent reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Heterocyclic Compounds / chemistry*
  • Imines / chemistry*
  • Lewis Acids / chemistry*
  • Molecular Structure
  • Quinolines / chemistry*
  • Stereoisomerism

Substances

  • Heterocyclic Compounds
  • Imines
  • Lewis Acids
  • Quinolines
  • 1,2,3,4-tetrahydroquinoline