Formal [4 + 1]-cycloaddition of homopropargyl alcohols to diazo dicarbonyl compounds giving substituted tetrahydrofurans

Org Lett. 2014 Feb 7;16(3):1004-7. doi: 10.1021/ol403746r. Epub 2014 Jan 13.

Abstract

A novel formal [4 + 1]-cycloaddition of readily available homopropargyl alcohols with diazo dicarbonyl compounds is described, which involves tandem O-H insertion/Conia-ene cyclization under cooperative Rh(II)/Zn(II) catalysis. This reaction provides easy access to various substituted tetrahydrofurans and exhibits complete E-selectivity in the case of nonterminal alkynes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Azo Compounds / chemical synthesis*
  • Azo Compounds / chemistry
  • Catalysis
  • Cycloaddition Reaction
  • Furans / chemistry*
  • Molecular Structure
  • Pargyline / analogs & derivatives*
  • Pargyline / chemistry*

Substances

  • Alcohols
  • Azo Compounds
  • Furans
  • Pargyline