Reaction of dimethoxycarbene-DMAD zwitterion with 1,2-diones and anhydrides: a novel synthesis of highly substituted dihydrofurans and spirodihydrofurans

J Org Chem. 2006 Mar 17;71(6):2313-9. doi: 10.1021/jo052429k.

Abstract

The zwitterion formed by the reaction of dimethoxycarbene and DMAD adds efficiently to one of the carbonyl groups of 1,2-dicarbonyl compounds and anhydrides to generate dihydrofurans and spirodihydrofurans in good yields. In many cases, the carbene inserts into the C-C bond of the dione to yield masked vicinal tricarbonyl systems.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Anhydrides / chemistry*
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Hydrocarbons / chemistry
  • Ketones / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Anhydrides
  • Furans
  • Hydrocarbons
  • Ketones
  • Spiro Compounds
  • carbene
  • acetylenedicarboxylic acid dimethyl ester
  • Methane