Morita-Baylis-Hillman reaction of lactams and lactones with alkyl halides and epoxides catalyzed by hydroxysulfides

Org Lett. 2010 May 21;12(10):2418-21. doi: 10.1021/ol100788g.

Abstract

A new Morita-Baylis-Hillman reaction methodology in which alkyl halides and epoxides act as electrophiles in their reaction with lactones and lactams is shown. Catalysis is efficiently performed by hydroxy sulfides under basic conditions. The procedure works efficiently with many alkyl halides but fails with aldehydes with which a conventional acid-catalyzed procedure is used.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Epoxy Compounds / chemistry*
  • Hydrocarbons, Halogenated / chemistry*
  • Lactams / chemistry*
  • Lactones / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Sulfides / chemistry*

Substances

  • Epoxy Compounds
  • Hydrocarbons, Halogenated
  • Lactams
  • Lactones
  • Sulfides