Separation tagging with cyclodextrin-binding groups: Mitsunobu reactions with bis-(2-(1-adatnantyl)ethyl) azodicarboxylate (BadEAD) and bis-(1-adamantylmethyl) azodicarboxylate (BadMAD)

被引：15

作者：

Dandapani, S ^{[1
]}

Newsome, JJ ^{[1
]}

Curran, DP ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 35期

基金：

美国国家卫生研究院;

关键词：

separation tagging; mitsunobu reaction; cyclodextrin;

D O I：

10.1016/j.tetlet.2004.07.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for separation tagging with cyclodextrin-binding groups is introduced and is exemplified in the context of the Mitsunobu reaction with adamantyl tags. HPLC experiments showed that molecules containing adamantyl groups were especially well retained on Sumichiral OA7500beta-methylated cyclodextrin bonded silica columns relative to many other types of molecules. Two new Mitsunobu reagents, bis-(1-adamantylmethyl) azodicarboxylate (BadMAD) and bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD), were prepared, used in typical Mitsunobu reactions and separated with both P-methylated cyclodextrin bonded silica and standard silica. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6653 / 6656

页数：4

共 23 条

[1] The 4-tert-butylphenyl group as a simple tag for solution phase synthesis [J].