Ligand-controlled gold-catalyzed cycloisomerization of 1,n-enyne esters toward synthesis of dihydronaphthalene

被引：36

作者：

Thummanapelli, Sravan K. ^{[1
]}

Hosseyni, Seyedmorteza ^{[2
]}

Su, Yijin ^{[1
]}

Akhmedov, Novruz G. ^{[1
]}

Shi, Xiaodong ^{[2
]}

机构：

[1] W Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA

[2] Univ S Florida, Dept Chem, Tampa, FL 33620 USA

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 49期

基金：

美国国家科学基金会;

关键词：

GOLD(I)-CATALYZED CYCLIZATION; ENANTIOSELECTIVE SYNTHESIS; CIS-DECAHYDROQUINOLINES; MOLECULAR COMPLEXITY; ASYMMETRIC-SYNTHESIS; ECONOMICAL SYNTHESIS; EFFICIENT SYNTHESIS; 2+2 CYCLOADDITION; 1,6-DIYNE ESTERS; TANDEM;

D O I：

10.1039/c6cc03032g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe herein a gold-catalyzed rearrangement of propargyl esters followed by allene-ene cyclization to afford substituted bicyclic [4.4.0] dihydronaphthalene compounds. This method is also applied to vinylethers and vinylamines of 1,7-enyne esters to form dihydroquinoline and dihydrobenzopyran structures. The basis of this transformation is the ligand-controlled preferential activation of the alkene over the allene, affording the desired aromatic bicyclic structures in moderate to excellent yields.

引用

页码：7687 / 7690

页数：4

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