The Synthesis of Stable, Complex Organocesium Tetramic Acids through the Ugi Reaction and Cesium-Carbonate-Promoted Cascades

Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11672-6. doi: 10.1002/anie.201504377. Epub 2015 Aug 12.

Abstract

Two structurally unique organocesium carbanionic tetramic acids have been synthesized through expeditious and novel cascade reactions of strategically functionalized Ugi skeletons delivering products with two points of potential diversification. This is the first report of the use of multicomponent reactions and subsequent cascades to access complex, unprecedented organocesium architectures. Moreover, this article also highlights the first use of mild cesium carbonate as a cesium source for the construction of cesium organometallic scaffolds. Relativistic DFT calculations provide an insight into the electronic structure of the reported compounds.

Keywords: Dieckmann condensation; Ugi reaction; cascade reactions; multicomponent reactions; tetramic acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonates / chemistry*
  • Cesium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Pyrrolidinones / chemistry*
  • Quantum Theory

Substances

  • Carbonates
  • Organometallic Compounds
  • Pyrrolidinones
  • Cesium
  • tetramic acid