Axially chiral analogues of 4-(dimethylamino)pyridine: Novel catalysts for nonenzymatic enantioselective acylations

被引：162
|
作者：
Spivey, AC [1 ]
Fekner, T [1 ]
Spey, SE [1 ]
机构：
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 10期
关键词：
D O I：
10.1021/jo0000574
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise seven-step synthesis of atropisomeric S-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (+/-)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity factors, s = 8.9-29).
引用
收藏
页码：3154 / 3159
页数：6
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