Rotaxanes amide based synthesis

V. Extending the Amide-Based Template Synthesis to Rotaxanes 18 7... 

The functionalisation also allows extending the complexity of intertwined molecular assemblies involving molecular catenanes, rotaxanes and knots. Elaborate interlocked assemblies constructed by means of metal-templation techniques and ji-ji-stacking preorganisation were reviewed [3, 11], Our last survey was devoted to the hydrogen bond templated synthesis of amide-based catenanes and rotaxanes [32], Since then a considerable advancement in elucidation of mechanisms of templation and derivatisation of the amide-based interlocked structures has been reached. Moreover, in 2000 we reported a one pot synthesis of amide-based knots such as 8 [21], which is so far the easiest preparation of molecular knots. In the following, specific possibilities of functionalisation of amide-based catenanes, rotaxanes and knots will be discussed. 

Template Synthesis of Amide-based Catenanes, Rotaxanes and Knots... 

The amide-based template synthesis of rotaxanes, catenanes and knots were first discovered by Vogtle and coworkers when they tried to synthesize macrocycle 3 [13], The cyclization to yield the tetralactam ring was carried out under high-dilution... 

Scheme 10 Synthesis of amide rotaxanes by a template effect based on the formation of...

The rotaxane is composed of a glycylglycine chain, a simple dipeptide, bearing two diphenylmethane blocking groups, which prevent the dethreading of the benzylic amide macrocycle. The synthesis of the rotaxane structure is based on... 

Replacement of one or both amide groups of the classical glycylglycine template for rotaxane formation with H-bond acceptors based on various P-containing functional groups resulted in effective motifs for the H-bond -directed synthesis of [2]rotaxanes. ... 

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