Mechanistic Studies on Au(I)-Catalyzed [3,3]-Sigmatropic Rearrangements using Cyclopropane Probes

被引：179
|
作者：
Mauleon, Pablo [1 ]
Krinsky, Jamin L. [1 ]
Toste, F. Dean [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 12期
关键词：
GOLD-CATALYZED CYCLOISOMERIZATION; BENT ACYCLIC ALLENE; PROPARGYLIC ESTERS; GOLD(I)-CATALYZED SYNTHESIS; EFFICIENT FORMATION; ENYNYL ACETATES; ACYL MIGRATION; TANDEM; ACCESS; CYCLOPROPYLCARBINYL;
D O I：
10.1021/ja900456m
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A comparative study of the Au(I)-catalyzed [3,3]-sigmatropic rearrangement of propargylic esters and propargyl vinyl ethers is described. Stereochemically defined cyclopropanes are employed as mechanistic probes to provide new synthetic and theoretical data concerning the reversibility of this type of rearrangement. Factors controlling the structure-reactivity relationship of Au(I)-coordinated allenes have been examined, thereby allowing for controlled access to orthogonal reactivity.
引用
收藏
页码：4513 / 4520
页数：8
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