Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols.
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.
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.
Longwu
L
Ye
Weimin
W
He
Liming
L
Zhang
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry*
D000480:Alkynes; D006573:Heterocyclic Compounds, 1-Ring; D020005:Propanols; D006046:Gold; C028255:propargyl alcohol