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Issue 22, 2009
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Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies

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Abstract

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.

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

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The article was received on 22 Jun 2009, accepted on 04 Aug 2009 and first published on 14 Sep 2009


Article type: Paper
DOI: 10.1039/B912189G
Citation: Org. Biomol. Chem., 2009,7, 4734-4743

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

    O. Plietzsch, C. I. Schilling, M. Tolev, M. Nieger, C. Richert, T. Muller and S. Bräse, Org. Biomol. Chem., 2009, 7, 4734
    DOI: 10.1039/B912189G

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