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

被引：260
作者：
Ye, Longwu [1 ]
He, Weimin [1 ]
Zhang, Liming [1 ]
机构：
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 25期
基金：
美国国家科学基金会;
关键词：
OXETANES;
D O I：
10.1021/ja1033952
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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 a-oxo metal carbene chemistry without using hazardous diazo ketones.
引用
收藏
页码：8550 / +
页数：3
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