Diastereo- and enantioselective direct vinylogous Michael addition of γ-substituted butenolides to 2-enoylpyridines catalyzed by chiral bifunctional amine-squaramides

Chem Commun (Camb). 2015 Nov 11;51(87):15835-8. doi: 10.1039/c5cc06383c.

Abstract

The diastereo- and enantioselective direct vinylogous Michael addition reaction of γ-substituted butenolides to 2-enoylpyridines has been achieved. A range of γ,γ-disubstituted butenolide derivatives, bearing two consecutive tri- and tetrasubstituted stereogenic centers, were readily obtained in good yields with excellent stereoselectivities (up to >99 : 1 dr and >99% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis*
  • 4-Butyrolactone / chemistry
  • Catalysis
  • Cyclobutanes / chemical synthesis*
  • Cyclobutanes / chemistry
  • Molecular Structure
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Stereoisomerism

Substances

  • Cyclobutanes
  • Pyridines
  • 4-Butyrolactone