Copper-Catalyzed [4+2] Cycloaddition of 9 H-Cyclohepta[ b]pyridine-9-one and Electron-Rich Alkenes

J Org Chem. 2019 Jul 5;84(13):8717-8723. doi: 10.1021/acs.joc.9b00899. Epub 2019 Jun 20.

Abstract

9 H-Cyclohepta[ b]pyridin-9-one was used as a diene cycloaddition partner to construct [3.2.2] bicycles in a copper-catalyzed [4+2] cycloaddition. Oxygen- and nitrogen-substituted terminal, disubstituted, trisubstituted, and cyclic alkenes reacted to afford the cycloadducts as single constitutional isomers in 48-80% yields and diastereomeric ratios up to 5.6:1.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry
  • Catalysis
  • Copper*
  • Cycloaddition Reaction*
  • Molecular Structure
  • Pyridones / chemical synthesis*
  • Pyridones / chemistry

Substances

  • Alkenes
  • Benzopyrans
  • Pyridones
  • Copper