Synthesis of Polyfluoroalkyl Cyclobutenes from 3-Aza-1,5-enynes via an Aza-Claisen Rearrangement/Cyclization Cascade

被引：18

作者：

Xin, Xiaoyi ^{[1
]}

Wang, Dongping ^{[1
]}

Wu, Fan ^{[1
]}

Wang, Chunxiang ^{[1
]}

Wang, Haolong ^{[1
]}

Li, Xincheng ^{[1
]}

Wan, Boshun ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 17期

基金：

中国国家自然科学基金;

关键词：

INTERMOLECULAR 2+2 CYCLOADDITION; PLATINUM-CATALYZED CYCLOISOMERIZATION; RING EXPANSION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; TERMINAL ALKYNES; ALKENES; FACILE; 1,1,3-TRIARYLPROP-2-YN-1-OLS; VINYLALLENES;

D O I：

10.1021/ol4020738

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthetic route to access polyfluoroalkyl functionalized cyclobutenes bearing an exo cyclic double bond from 3-aza-1,5-enynes is reported. The reaction proceeds via a thermal aza-Claisen rearrangement to give an allene-imine intermediate; subsequent cyclization affords the cyclobutene core. The kinetics of the transformation of starting material and the intermediate was studied by H-1 NMR spectroscopy, where a consecutive reaction was revealed.

引用

页码：4512 / 4515

页数：4

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