Issue 21, 2017

Enhanced site-selectivity in acylation reactions with substrate-optimized catalysts on solid supports

Abstract

A concept for site selective acylation of poly-hydroxylated substrates is presented where polymer-supported catalysts are employed: catalytically active DMAP units were combined with a library of small molecule peptides attached to the solid phase with the goal to identify substrate-optimized catalysts through library screening. For selected examples, we demonstrate how the optimized catalysts can convert “their” substrate with a markedly enhanced site-selectivity, compared to only DMAP. Due to the solid support, product purification is significantly simplified, and the peptidic catalysts can be easily reused in multiple cycles while conserving its efficiency.

Graphical abstract: Enhanced site-selectivity in acylation reactions with substrate-optimized catalysts on solid supports

Supplementary files

Article information

Article type
Communication
Submitted
23 Jan 2017
Accepted
20 Feb 2017
First published
28 Feb 2017

Chem. Commun., 2017,53, 3086-3089

Enhanced site-selectivity in acylation reactions with substrate-optimized catalysts on solid supports

M. L. Tong, F. Huber, E. S. Taghuo Kaptouom, T. Cellnik and S. F. Kirsch, Chem. Commun., 2017, 53, 3086 DOI: 10.1039/C7CC00655A

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