Copper-Catalyzed [2+3] Cyclization of α-Hydroxyl Ketones and Arylacetonitriles: Access to Multisubstituted Butenolides and Oxazoles

被引：23

作者：

Qi, Chaorong ^{[1
,2
]}

Peng, Youbin ^{[1
]}

Wang, Lu ^{[1
]}

Ren, Yanwei ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China

[2] South China Univ Technol, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; 2,5-DISUBSTITUTED OXAZOLES; OXIDATIVE CYCLIZATION; SUBSTITUTED BUTENOLIDES; CLEAVAGE REACTIONS; ANNULATION; BOND; GOLD; NITRILES; ROUTE;

D O I：

10.1021/acs.joc.8b01822

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed [2 + 3] formal cyclization reaction between alpha-hydroxyl ketones and arylacetonitriles has been developed. The reaction outcome was ultimately dependent on the structure of the alpha-hydroxy ketones employed. Tertiary alpha-hydroxy ketones gave 3,4,5,5-tetrasubstituted butenolides as the sole products, while secondary alpha-hydroxy ketones furnished 2,4,5-trisubstituted oxazoles selectively. This method has many advantages, such as the use of easily available substrates, broad substrate scope, good functional tolerance, and milder reaction conditions.

引用

页码：11926 / 11935

页数：10

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