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Issue 5, 2016
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Competition-driven selection in covalent dynamic networks and implementation in organic reactional selectivity

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Abstract

Competition among reagents in dynamic combinatorial libraries of increased complexity leads to reactional self-sorting (improved regioselectivity) in mixtures of aldehydes and oligoamines. High selectivity of a given library component is transferred to a different reacting component of low selectivity through a network of underlying equilibrating reactions which provide component exchange between all species. The selectivity of various carbonyl compounds in reactions with amines was also assessed towards the formation of defined sequences of residues along oligoamine chains. The approach was further exploited for defining selective dynamic protecting groups (DPGs), based on the reversible linkage between the substrate and the protecting group. They represent an intermediate approach between the conventional protecting groups and the protecting-group-free approach in organic synthesis. Removal of the protecting group is effected via dynamic exchange trapping by formation of a more stable product. The establishment of equilibrium eliminates the need for isolation and purification of the dynamically protected intermediate(s) and enables as well the selective sequential derivatisation of oligoamines. The DPG concept can be generalised to other reversible reactions and can thus represent a valuable alternative in the design of total synthesis of complex molecules.

Graphical abstract: Competition-driven selection in covalent dynamic networks and implementation in organic reactional selectivity

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Supplementary files

Article information


Submitted
24 Aug 2015
Accepted
03 Feb 2016
First published
10 Feb 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 3215-3226
Article type
Edge Article
Author version available

Competition-driven selection in covalent dynamic networks and implementation in organic reactional selectivity

P. Kovaříček, A. C. Meister, K. Flídrová, R. Cabot, K. Kovaříčková and J.-M. Lehn, Chem. Sci., 2016, 7, 3215
DOI: 10.1039/C5SC04924E

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