Deuterium-labeling studies establishing stereochemistry at the oxypalladation step in Wacker-type oxidative cyclization of an o-allylphenol

被引:108
作者
Hayashi, T [1 ]
Yamasaki, K [1 ]
Mimura, M [1 ]
Uozumi, Y [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
关键词
D O I
10.1021/ja031946m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stereochemical pathway (syn or anti) of the oxypalladation step was studied in the palladium(II)-catalyzed Wacker-type cyclization of stereospecifically deuterated 6-(2-hydroxyphenyl)-3-deuteriocyclohexenes, cis-3-d-1 and trans-3-d-1, giving dihydrobenzofuran derivatives. The stereochemistry was determined to be syn in the reaction catalyzed by a dicationic palladium(II) catalyst generated from Pd(MeCN)4(BF4)2 and (S,S)-ip-boxax in the presence of benzoquinone in methanol, while it is mainly anti in the reaction catalyzed by PdCl2(MeCN)2 in the presence of a chloride ion. Copyright © 2004 American Chemical Society.
引用
收藏
页码:3036 / 3037
页数:2
相关论文
共 31 条