Stereoselective preparation of functionalized unsaturated lactones and esters via functionalized magnesium carbenoids

被引：26
|
作者：
Vu, VA
Marek, I
Knochel, P
机构：
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
[2] Technion Israel Inst Technol, Dept Chem, IL-32000 Technion, Haifa, Israel
来源：
SYNTHESIS-STUTTGART | 2003年 / 12期
关键词：
functionalized magnesium carbenoids; iodine-magnesium exchange; cross-coupling; lactone synthesis; palladium catalysis;
D O I：
10.1055/s-2003-41035
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of beta,beta-dibromo or diiodo unsaturated esters with i-PrMgCl (I equivalent) in diethyl ether allows the generation of functionalized alkenylmagnesium carbenoids which react with retention of configuration with various electrophiles providing polyfunctionalized unsaturated esters and lactones. By using two equivalents of i-PrMgCl, a 1,2-migration with retention of configuration occurs in diethyl ether allowing a new synthesis of tetrasubstituted esters and lactones.
引用
收藏
页码：1797 / 1802
页数：6
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