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

被引：119

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.

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收藏

页码：1250 / 1253

页数：4

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