Triflic Acid-Catalyzed Cycloisomerization Reactions of Donor-Acceptor Cyclopropanes: Access to Alkyl 5-Arylfuran-2-carboxylates

被引：14

作者：

Zhu, Yuequan ^{[1
]}

Xu, Panpan ^{[1
]}

Gong, Yuefa ^{[1
]}

机构：

[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, 1037 Luoyu Rd, Wuhan 430074, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 11期

基金：

中国国家自然科学基金;

关键词：

DOMINO REACTIONS; DIASTEREOSELECTIVE SYNTHESIS; 2,5-DISUBSTITUTED FURANS; SUBSTITUTED FURANS; EFFICIENT; CYCLOADDITIONS; PYRROLIDINES; ALDEHYDES; SEQUENCE; IMINES;

D O I：

10.1021/acs.joc.6b00161

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct synthetic strategy starting from alkyl 1-alkoxy-2-aroylcyclopropanecarboxylates was developed for the construction of alkyl 5-arylfuran-2-carboxylates. These donor acceptor cyclopropanes smoothly undergo a simple ring opening reaction or/and cycloisomerization reaction in the presence of acid at room temperature;, which greatly depends on the properties of the acid used in the experiment, Alkyl 5-arylfuran-2-carboxylates were afforded in high yields in triflic acid, whereas alkyl 2,5-dioxo-5-phenylpentanoate became the major product in other protic acids and Lewis acids.

引用

页码：4829 / 4834

页数：6

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