Enantioselective Gold(I)-Catalyzed Vinylogous [3+2] Cycloaddition between Vinyldiazoacetates and Enol Ethers

被引：102
|
作者：
Briones, John F. [1 ]
Davies, Huw M. L. [1 ]
机构：
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 36期
基金：
美国国家科学基金会;
关键词：
BOND FUNCTIONALIZATION; CATALYZED CYCLIZATION; CARBENE INSERTION; CYCLOPROPANATION; REACTIVITY; CYCLOISOMERIZATIONS; HYDROAMINATION; REARRANGEMENT; COMPLEXES; AU;
D O I：
10.1021/ja407179c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The reaction of vinyldiazoacetates with enol ethers catalyzed by the binuclear gold complex (R)-DTBMSegphos(AuCl)(2) activated by silver hexafluoroantimonate results in a highly enantioselective [3 + 2] cycloaddition. The [3 + 2] cycloaddition proceeds with dynamic kinetic resolution when the enol ether is a 4-substituted 1-(methoxymethylene)cyclohexane. The reaction is initiated by nucleophilic attack of the vinyl ethers at the vinylogous position of the gold vinylcarbene intermediate.
引用
收藏
页码：13314 / 13317
页数：4
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