Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies

被引：71

作者：

Plietzsch, Oliver ^{[1
,2
]}

Schilling, Christine Inge ^{[1
,2
]}

Tolev, Mariyan ^{[1
,2
,3
]}

Nieger, Martin ^{[4
]}

Richert, Clemens ^{[1
,2
,3
]}

Muller, Thierry ^{[1
,2
]}

Braese, Stefan ^{[1
,2
]}

机构：

[1] Univ Karlsruhe TH, Inst Organ Chem, KIT, D-76131 Karlsruhe, Germany

[2] Univ Karlsruhe TH, CFN, KIT, D-76131 Karlsruhe, Germany

[3] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

[4] Univ Helsinki, Inorgan Chem Lab, FIN-00014 Helsinki, Finland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 22期

关键词：

HYDROGEN-BONDED NETWORKS; 1,3-DIPOLAR CYCLOADDITIONS; CONVENIENT SYNTHESES; CRYSTAL-STRUCTURE; ORGANIC AZIDES; ONE-POT; CHEMISTRY; TECTONICS; DESIGN; DERIVATIVES;

D O I：

10.1039/b912189g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modular concept for the generation of achiral and chiral non-racemic tetrahedral tectons from common precursors was developed. The tectons presented here are based on tetraphenylmethane or 1,3,5,7-tetraphenyladamantane core structures. They are obtained through high-yielding four-fold click reactions, using either the tetraazido or the tetraalkyne precursors. In most cases, the tetratriazoles are obtained as pure products after simple washing with water and methanol. The side chains of the tectons prepared include a self-complementary DNA dimer, obtained from a 3'-azidonucleoside and a phosphoramidite. The concept allows for a variation of the "sticky ends", leading to tecton or ligand libraries.

引用

页码：4734 / 4743

页数：10

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