Gold-Catalyzed Highly Regioselective Oxidation of C-C Triple Bonds without Acid Additives: Propargyl Moieties as Masked α,β-Unsaturated Carbonyls

被引：177

作者：

Lu, Biao ^{[1
]}

Li, Chaoqun ^{[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 / 40期

基金：

美国国家科学基金会;

关键词：

ONE-POT SYNTHESIS; ALKYNES; KETONES; ACETYLENES; CYCLOPROPANATION; ORGANOSTANNANES; CYCLOADDITION; 1,2-DIKETONES; REARRANGEMENT; INTERMEDIATE;

D O I：

10.1021/ja1072614

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Gold-catalyzed intermolecular oxidations of internal alkynes have been achieved with high regioselectivities using 8-alkylquinoline N-oxides as oxidants and in the absence of acid additives. Synthetically versatile a,beta-unsaturated carbonyls are obtained in good to excellent yields and with excellent E-selectivities. A range of functional groups such as THP, MOMO, N-3, OTBS, and N-Boc are tolerated. This reaction allows alpha,beta-unsaturated carbonyls to be masked as propargyl moieties, thus offering a practical solution to compatibility issues with these functional groups likely encountered in syntheses of complex structures.

引用

页码：14070 / 14072

页数：3

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