Resolution and coupling of 1-(2′-hydroxy-1′-naphthyl)isoquinolines

被引：29
|
作者：
Tucker, SC
Brown, JM
Oakes, J
Thornthwaite, D
机构：
[1] Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Unilever Res Labs, Wirral L63 3JW, Merseyside, England
来源：
TETRAHEDRON | 2001年 / 57卷 / 13期
基金：
英国工程与自然科学研究理事会;
关键词：
racemisation; enantiomers; palladocycles; isoquinolines; atropisomerism;
D O I：
10.1016/S0040-4020(01)00064-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of bridged dimeric isoquinolylnaphthols has been developed. A simple method for the resolution of 1,1'-isoquinolyl-2'-naphthol permits measurement of the optical stability of the monomer, and in several cases slow racemisation at ambient temperature was observed. The enantiomeric stability is not greatly affected by steric buttressing. An unusual enhancement of the rate of atropisomerism is provided by the 3-bromomethylisoquinolines, and undermines the possibility of coupling pure enantiomeric components to provide a single stereoisomer of a tetradentate ligand. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2545 / 2554
页数：10
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