Palladium-Catalyzed Intermolecular Oxyvinylcyclization of Alkenes with Alkynes: An Approach to 3-Methylene γ-Lactones and Tetrahydrofurans

被引：54
|
作者：
Zhang, Zhenming [1 ]
Ouyang, Lu [1 ]
Wu, Wanqing [1 ]
Li, Jianxiao [1 ]
Zhang, Zhicai [1 ]
Jiang, Huanfeng [1 ]
机构：
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 22期
基金：
中国国家自然科学基金;
关键词：
STEREOSELECTIVE-SYNTHESIS; IONIC LIQUIDS; CARBOAMINATION REACTIONS; REGIOSELECTIVE SYNTHESIS; OXIDATIVE CYCLIZATION; HIGHLY REGIO; PRODUCT STEREOCHEMISTRY; INDOLE-DERIVATIVES; TERMINAL ALKYNES; C-C;
D O I：
10.1021/jo501606c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel chloropalladation-initiated intermolecular oxyvinylcyclization of alkenes with alkynoic acids or alkynols is developed. This protocol provides a series of 3-methylene γ-lactone and tetrahydrofuran derivatives in moderate to excellent yields with high stereoselectivities in the presence of PdCl2 and CuCl2 or CuCl2·2H2O. Besides a broad substrate scope, this method has the advantages of mild reaction conditions and easily accessible starting materials. Furthermore, the construction of C-Cl, C(sp2)-C(sp3), and C-O bonds in one step was also achieved in this transformation. © 2014 American Chemical Society.
引用
收藏
页码：10734 / 10742
页数：9
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