Synthesis and separation of the atropisomers of 2-(5-benzo[b]fluorenyl)-2′-hydroxy-1,1′-binaphthyl and related compounds

被引：6
|
作者：
Yang, Hua [1 ]
Petersen, Jeffrey L. [1 ]
Wang, Kung K. [1 ]
机构：
[1] W Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA
来源：
TETRAHEDRON | 2006年 / 62卷 / 34期
基金：
美国国家科学基金会;
关键词：
2-(5-benzo[b]fluorenyl)-2 '-hydroxy-1,1 '-binaphthyls; atropisomers; benzannulated enyne-allenes; cascade biradical cyclization;
D O I：
10.1016/j.tet.2006.06.004
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several syn and anti atropisomers of 2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl and related compounds were synthesized from 1,1'-binaphthyl-2,2'-diol (BINOL). It was possible to separate the syn and anti atropisomers by silica gel column chromatography. The syn atropisomers are potential hetero-bidentate ligands for complex formation with metals. By starting from enantiomerically pure (R)-(+)-BINOL and (S)-(-)-BINOL, four optically active syn atropisomers and two anti atropisomers with high enantiomeric purity were obtained. The structures of two syn atropisomers and one anti atropisomer were established by X-ray structure analyses. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8133 / 8141
页数：9
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