A new class of chiral PN-ligands and their application in palladium-catalyzed asymmetric allylic substitution reactions

被引：28

作者：

Lyle, MPA ^{[1
]}

Narine, AA ^{[1
]}

Wilson, PD ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 15期

关键词：

D O I：

10.1021/jo0494275

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and modular synthesis of a series of chiral nonracemic PN-ligands is reported. The P,N-ligands were prepared from 2-chloro-4-methyl-6,7-dihydro-5H-[1]pyrindine-7-one and a series of substituted chiral C-2-symmetric 1,2-ethanediols (R = Me, i-Pr, and Ph). The ligands were evaluated for use in catalytic asymmetric synthesis in the palladium-catalyzed allylic substitution reactions of a racemic allylic acetate and dimethyl malonate. In the case of the P,N-ligand (R = Ph), the reaction was found to be highly stereoselective (90% ee).

引用

页码：5060 / 5064

页数：5

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