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
收藏
页码：2122 / 2125
页数：4
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