Bronsted acid catalyzed asymmetric reduction of 2- and 2,9-substituted 1,10-phenanthrolines

被引：41
|
作者：
Metallinos, Costa [1 ]
Barrett, Fred B. [1 ]
Xu, Shufen [1 ]
机构：
[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada
来源：
SYNLETT | 2008年 / 05期
关键词：
reduction; phenanthroline; Bronsted acid; enantioselective; organocatalysis;
D O I：
10.1055/s-2008-1032103
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several 2- and 2,9-substituted 1,10-phenanthrolines are reduced asymmetrically for the first time using a Hantzsch dihydropyridine in the presence of BINOL-derived phosphoric acid catalysts. The best results are obtained with phenanthrolines bearing unbranched or nitrogen-containing alkyl groups in the 2- or 2,9-positions, which afford chiral octahydrophenanthrolines in a range of yields (40-88%) and good to excellent levels of enantiomeric purity (78-99% ee).
引用
收藏
页码：720 / 724
页数：5
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