Design, Synthesis, and Evaluation of a Helicenoidal DMAP Lewis Base Catalyst

被引：118
作者：
Crittall, Matthew R. [1 ]
Rzepa, Henry S. [2 ]
Carbery, David R. [1 ]
机构：
[1] Univ Bath, Dept Chem, Bath, Avon, England
[2] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 05期
基金：
英国工程与自然科学研究理事会;
关键词：
KINETIC RESOLUTION; SECONDARY ALCOHOLS; 4-(DIALKYLAMINO)PYRIDINES; CYCLOADDITIONS; ACYLATION; ORIGIN;
D O I：
10.1021/ol2001705
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The design, synthesis, and study of a helical dialkylaminopyridine Lewis base catalyst is reported. Helical DMAP analogue 4 is based upon a helicenoid structure and displays good to excellent levels of selectivity (S <= 116) in the kinetic resolution of chiral secondary alcohols. Catalyst 4 displays excellent reactivity with exceptionally low loadings of 0.05 mol % effecting practical levels of selectivity in kinetic resolutions.
引用
收藏
页码：1250 / 1253
页数：4
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