Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers

被引：64

作者：

Shen, Hang ^{[1
]}

Li, Jiaqiang ^{[1
]}

Liu, Qing ^{[1
]}

Pan, Jing ^{[1
]}

Huang, Ruofeng ^{[1
]}

Xiong, Yan ^{[1
,2
]}

机构：

[1] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400044, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 14期

基金：

中国国家自然科学基金;

关键词：

BORON-TRIFLUORIDE ETHERATE; LEWIS-ACID CONDITIONS; ENANTIOSELECTIVE CYANOSILYLATION; PHARMACOLOGICAL EVALUATION; CONVENIENT SYNTHESIS; ALDEHYDES; KETONES; OXIDATION; CHEMISTRY; CYANO;

D O I：

10.1021/acs.joc.5b01102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method to synthesize beta-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3 center dot Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

引用

页码：7212 / 7218

页数：7

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