Carbonylation of epoxides to substituted 3-hydroxy-delta-lactones

Org Lett. 2007 Dec 20;9(26):5581-3. doi: 10.1021/ol702475e. Epub 2007 Nov 21.

Abstract

Substituted 3-hydroxy-delta-lactones (3HLs) are valuable intermediates in the synthesis of pharmaceuticals and other biologically active natural products. Herein we report the first example of the catalytic carbonylation of substituted homoglycidols to 3HLs using HCo(CO)4. Upon optimization of the catalyst and reaction conditions, a functionally diverse set of 3HLs was prepared. Mechanistic insight was gained by observation of the carbonylation reaction using in situ IR spectroscopy, and we propose a mechanism that is consistent with previously studied epoxide carbonylation systems.

Publication types

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

MeSH terms

  • Epoxy Compounds / chemistry*
  • Ketones / chemistry*
  • Lactones / chemistry*
  • Spectrophotometry, Infrared

Substances

  • Epoxy Compounds
  • Ketones
  • Lactones