1,2-aryl and 1,2-hydride migration in transition metal complex catalyzed diazo decomposition:: A novel approach to α-aryl-β-enamino esters

被引：125
|
作者：
Jiang, N [1 ]
Qu, ZH [1 ]
Wang, JB [1 ]
机构：
[1] Beijing Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Edu, Dept Chem, Beijing 100871, Peoples R China
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 19期
关键词：
D O I：
10.1021/ol016324p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] N-Tosyl diazoketamines were prepared by addition of the ethyl alpha -diazoacetate anion to N-sulfonylimines. The diazo decomposition of the diazoketamines with Rh-2(OAc)(4) complex resulted in aryl migration to give alpha -aryl-beta -enamino esters in good yields and high stereoselectivity. The effect of the catalysts on the migratory aptitude of 1,2-aryl over 1,2-hydride migration was studied. A reaction mechanism involving a "bridged" phenonium ion is proposed.
引用
收藏
页码：2989 / 2992
页数：4
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