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

页码：8550 / +

页数：3

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