Unexpected effect of the fluorine atom on the optimal ligand-to-palladium ratio in the enantioselective Pd-catalyzed allylation reaction of fluorinated enol carbonates

被引：65

作者：

Belanger, Etienne ^{[1
]}

Houze, Clement ^{[1
]}

Guimond, Nicolas ^{[1
]}

Cantin, Katy ^{[1
]}

Paquin, Jean-Francois ^{[1
]}

机构：

[1] Univ Laval, Dept Chim, Canada Res Chair Organ & Med Chem, Quebec City, PQ G1V 0A6, Canada

来源：

CHEMICAL COMMUNICATIONS | 2008年 / 28期

关键词：

D O I：

10.1039/b803097a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective Pd-catalyzed allylation reaction of fluorinated allyl enol carbonates is presented; a key feature of this transformation is the important effect of the ligand-to-palladium ratio on the enantioselectivity of the alpha-fluoroketones, since using a ligand excess (L/Pd ratio = 1.25 : 1) led to moderate results (30-76% ee), while using a L/Pd ratio <1 : 1.67 (to as low as 1 : 4) allowed the desired products to be obtained with high enantiopurity (up to 94% ee).

引用

页码：3251 / 3253

页数：3

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