Unprecedented ligand dependent SN2′ mechanism on the palladium-catalyzed nucleophilic substitution to bicyclic dienyl acetates

被引：3

作者：

Daimon, H ^{[1
]}

Kitamura, T ^{[1
]}

Kawahara, T ^{[1
]}

Shimizu, I ^{[1
]}

机构：

[1] Waseda Univ, Sch Sci & Engn, Dept Appl Chem, Shinjuku Ku, Okubo 3-4-1, Tokyo 1698555, Japan

来源：

CHEMISTRY LETTERS | 2005年 / 34卷 / 03期

关键词：

D O I：

10.1246/cl.2005.408

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium-catalyzed nucleophilic reaction to bicyclic dienyl acetates 1 was studied with both optically active substrates and deuterium labeled substrates in order to clarify regioselectivity of the reaction. The regioselectivity depended on phosphine ligands. Thus, S(N)2 type reaction was observed using PPh3. Whereas, unprecedented S(N)2' type reaction proceeded in high yields using DPPP and DPPB, which is applicable to a remote nucleophilic substitution.

引用

页码：408 / +

页数：2

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