Rhodium(II)-catalyzed enantioselective synthesis of troponoids

Angew Chem Int Ed Engl. 2015 Jun 22;54(26):7653-6. doi: 10.1002/anie.201502233. Epub 2015 May 8.

Abstract

We report a rhodium(II)-catalyzed highly enantioselective 1,3-dipolar cycloaddition reaction between the carbonyl moiety of tropone and carbonyl ylides to afford troponoids in good to high yields with excellent enantioselectivity. We demonstrate that α-diazoketone-derived carbonyl ylides, in contrast to carbonyl ylides derived from diazodiketoesters, undergo [6+3] cycloaddition reactions with tropone to yield the corresponding bridged heterocycles with excellent stereoselectivity.

Keywords: asymmetric catalysis; carbonyl ylides; cycloaddition; rhodium; tropone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemical synthesis*
  • Catalysis
  • Cycloaddition Reaction
  • Molecular Structure
  • Rhodium / chemistry*
  • Stereoisomerism
  • Tropolone / analogs & derivatives*
  • Tropolone / chemistry

Substances

  • Azo Compounds
  • Tropolone
  • tropone
  • Rhodium