Gold-Catalyzed One-Step Practical Synthesis of Oxetan-3-ones from Readily Available Propargylic Alcohols

• Published in: Journal of the American Chemical Society Vol. 132; no. 25; pp. 8550 - 8551
• Main Authors: Ye, Longwu, He, Weimin, Zhang, Liming
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 30.06.2010; Amer Chemical Soc
• Subjects: Alkynes - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Gold - chemistry; Heterocyclic Compounds, 1-Ring - chemical synthesis; Heterocyclic Compounds, 1-Ring - chemistry; Oxidation-Reduction; Physical Sciences; Propanols - chemistry; Science & Technology; OXETANES
• ISSN: 0002-7863; 1520-5126; 1520-5126
• DOI: 10.1021/ja1033952

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 α-oxo gold carbenes. This safe and efficient generation of gold carbenes via intermolecular alkyne oxidation offers a potentially general entry into α-oxo metal carbene chemistry without using hazardous diazo ketones.