Exploiting dense shell/packing principles to invoke stereoselectivity in a reaction accelerated by a chiral dendrimer

Adam Ellis,Lance J Twyman,Melanie Wallace

doi:10.1039/c3cc43830a

Adam Ellis, Lance J Twyman + Show 1 more

Open Access

https://doi.org/10.1039/c3cc43830a

Copy DOI

Abstract

As dendrimers approach their dense shell or dense packed limit, a certain amount of conformational organization exists. Any substrate binding within the dendrimer's external layer will experience the same organizational effects. This paper describes how these effects can be exploited towards stereocontrol with respect to binding and reactivity.

Highlights

As dendrimers approach their dense shell or dense packed limit, a certain amount of conformational organization exists
The fastest reaction was observed for the dendrimer with 32 terminal amine groups (3rd generation)
We describe the aminolysis of hydrophobic Boc-protected L and D phenyl aniline using a 3rd generation water-soluble dendrimer terminated with nucleophilic L-phenylalanine groups

Summary

Introduction

As dendrimers approach their dense shell or dense packed limit, a certain amount of conformational organization exists. The fastest reaction was observed for the dendrimer with 32 terminal amine groups (3rd generation).

Results

Conclusion