Gosteli-Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements

被引：28

作者：

Gille, Annika ^{[1
]}

Rehbein, Julia ^{[1
]}

Hiersemann, Martin ^{[1
]}

机构：

[1] Tech Univ Dortmund, Fak Chem, D-44227 Dortmund, Germany

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 08期

关键词：

DENSITY-FUNCTIONAL THERMOCHEMISTRY; GOLD(I)-CATALYZED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SOLVENTS;

D O I：

10.1021/ol200558j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ambivalent reactivity of 2-alkoxycarbonyl-substituted propargyl vinyl ethers has been explored. Depending on the conditions, the catalyzed and uncatalyzed Gosteli-Claisen rearrangement triggers downstream transformations that cascade from initially formed gamma-allenyl alpha-keto esters to highly substituted furanes and cyclopentenes. In support of a mechanistic hypothesis, the results of a DFT study using the B1B95 and B3LYP functionals are revealed.

引用

页码：2122 / 2125

页数：4

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