钯催化的烯烃与炔烃的分子间氧乙烯基环化反应：一种合成3-亚甲基γ-内酯和四氢呋喃的方法。

Palladium-catalyzed intermolecular oxyvinylcyclization of alkenes with alkynes: an approach to 3-methylene γ-lactones and tetrahydrofurans.

作者信息

Zhang Zhenming, Ouyang Lu, Wu Wanqing, Li Jianxiao, Zhang Zhicai, Jiang Huanfeng

机构信息

School of Chemistry and Chemical Engineering, South China University of Technology , Guangzhou 510640, P. R. China.

出版信息

J Org Chem. 2014 Nov 21;79(22):10734-42. doi: 10.1021/jo501606c. Epub 2014 Sep 22.

DOI:10.1021/jo501606c

PMID:25215554

Abstract

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(sp(2))-C(sp(3)), and C-O bonds in one step was also achieved in this transformation.

摘要

开发了一种由新型氯钯化引发的烯烃与炔酸或炔醇的分子间氧乙烯基环化反应。该方法在PdCl2和CuCl2或CuCl2·2H2O存在下，能以中等至优异的产率和高立体选择性提供一系列3-亚甲基γ-内酯和四氢呋喃衍生物。除了底物范围广泛外，该方法还具有反应条件温和、起始原料易于获得的优点。此外，该转化反应还实现了一步构建C-Cl、C(sp(2))-C(sp(3))和C-O键。