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

页码：2231 / 2234

页数：4

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