Gold-Catalyzed Tandem 1,3-Migration/Double Cyclopropanation of 1-Ene-4,n-diyne Esters to Tetracyclodecene and Tetracycloundecene Derivatives

被引：35

作者：

Chen, Cuili ^{[1
]}

Zou, Yongzhen ^{[1
]}

Chen, Xianxiao ^{[1
]}

Zhang, Xiaoxiang ^{[1
]}

Rao, Weidong ^{[1
]}

Chan, Philip Wai Hong ^{[2
,3
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Jiangsu, Peoples R China

[2] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

[3] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 18期

基金：

中国国家自然科学基金; 澳大利亚研究理事会;

关键词：

PROPARGYLIC ESTERS; ENYNE CYCLOISOMERIZATION; 1,6-DIYNE CARBONATES; MOLECULAR COMPLEXITY; PLATINUM CATALYSIS; REARRANGEMENT; CYCLOADDITIONS; CYCLIZATION; MIGRATION; ACETATES;

D O I：

10.1021/acs.orglett.6b02404

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic method that relies on Au(I)-catalyzed tandem 1,3-acyloxy migration/double cyclopropanation of 1-ene-4,9-diyne and 1-ene-4,10-diyne esters to construct the respective architecturally challenging tetracyclodecene and tetracycloundecene derivatives is described. Achieved under mild reaction conditions, the transformation was shown to be robust with a wide variety of substitution patterns tolerated to give the two members of the carbocyclic family in good to excellent yields and as a single regio- and diastereomer.

引用

页码：4730 / 4733

页数：4

共 17 条

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