A palladium-catalyzed sequence of allylic alkylation and Hiyama cross-coupling:: Convenient synthesis of 4-(α-styryl) γ-lactones

被引：11
|
作者：
Vitale, Maxime [1 ]
Prestat, Guillaume [1 ]
Lopes, David [1 ]
Madec, David [1 ]
Poli, Giovanni [1 ]
机构：
[1] Univ Paris 06, Lab Chim Organ, CNRS, UMR 7611,Inst Chim Mol FR2769, F-75252 Paris, France
来源：
SYNLETT | 2006年 / 14期
关键词：
palladium; allylic alkylations; Hiyama cross-coupling; lactones; ring closure;
D O I：
10.1055/s-2006-949651
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Unsaturated malonyl esters underwent Pd-catalyzed intramolecular allylic alkylation to give 4-vinyl -substituted gamma-lactones. In contrast to the previously studied cyclization of malonamides, this reaction could only be achieved with a substrate incorporating ajudiciously positioned silicon moiety, which directs the ionization toward the desired eta(3)-allyl-palladium complex. The resulting 4-[dimethyl(2-thienyl)silylvinyl]lactone could be subsequently engaged into Hiyama couplings to give the corresponding 4-(alpha-styryl) gamma-lactones.
引用
收藏
页码：2231 / 2234
页数：4
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