Mechanistic investigations in diastereoselective Diels-Alder additions of chiral 9-anthrylethanol derivatives

被引:29
作者
Atherton, JCC [1 ]
Jones, S [1 ]
机构
[1] Newcastle Univ, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 19期
关键词
D O I
10.1039/b206523a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation and subsequent Diels-Alder addition reactions of chiral 9-functionalised anthracene derivatives have been investigated. 9-(1-Methoxyethyl) anthracene undergoes highly diastereoselective (> 95 : 5) thermal and photoinduced Diels-Alder additions with maleic anhydride and N-methylmaleimide. The corresponding reactions of 1-anthracen-9-ylethanol occur with the reverse sense of selectivity for additions with maleic anhydride with a corresponding increase in the reaction rate. The origins of this selectivity have been proposed to lie in hydrogen-bonding effects. The stereochemical outcome of the Diels-Alder additions has been determined from single X-ray crystallography of adducts 5 and 7. Solvent effects on the diastereoselectivity of these reactions have also been observed.
引用
收藏
页码:2166 / 2173
页数:8
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