Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols

J Am Chem Soc. 2010 Jun 30;132(25):8550-1. doi: 10.1021/ja1033952.

Abstract

A general solution for the synthesis of various oxetan-3-ones is developed. This reaction uses readily available propargylic alcohols as substrates and proceeds without the exclusion of moisture or air ("open flask"). Notably, oxetan-3-one, a highly valuable substrate for drug discovery, can be prepared in one step from propargyl alcohol in a fairly good yield. The facile formation of the strained oxetane ring provides strong support for the intermediacy of alpha-oxo gold carbenes. This safe and efficient generation of gold carbenes via intermolecular alkyne oxidation offers a potentially general entry into alpha-oxo metal carbene chemistry without using hazardous diazo ketones.

Publication types

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

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Gold / chemistry*
  • Heterocyclic Compounds, 1-Ring / chemical synthesis*
  • Heterocyclic Compounds, 1-Ring / chemistry*
  • Oxidation-Reduction
  • Propanols / chemistry*

Substances

  • Alkynes
  • Heterocyclic Compounds, 1-Ring
  • Propanols
  • Gold
  • propargyl alcohol