Atropisomerism of the C-1-C′-1 axis of 2,2′,8,8′-unsubstituted 1,1′-binaphthyl derivatives

被引:16
作者
Chow, HF [1 ]
Wan, CW [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
关键词
D O I
10.1021/jo0100289
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Suzuki coupling of optically active (S)-binaphthyl bromide 10 with (S)-binaphthyl boronic acid 11 produced a diastereomeric mixture of tetrahydroxyquaternaphthyls 4. The coupling products 4 as well as their derivatives 5-7 can be considered as members of the family of 1,1 ' -binaphthyl-3,3 ' -diols. The C-1-C ' -1 axis of all these compounds was found to have an unusually high rotational barrier. Generally, the barrier is higher for derivatives having more bulky substituents at the 3 and 3 ' positions.
引用
收藏
页码:5042 / 5047
页数:6
相关论文
共 17 条