Chiral Amphiphilic Secondary Amine-Porphyrin Hybrids for Aqueous Organocatalysis

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2020 Aug 1

PMID 32731520

Citations 10

Authors

Aitor Arlegui

Pol Torres

Victor Cuesta

Joaquim Crusats

Albert Moyano

Affiliations

Soon will be listed here.

Abstract

Two chiral proline-derived amphiphilic 5-substituted-10,15,20-tris(4-sulfonatophenyl)porphyrins were prepared, and their pH-dependent supramolecular behavior was studied. In neutral aqueous solutions, the free-base form of the hybrids is highly soluble, allowing enamine-based organocatalysis to take place, whereas under acidic conditions, the porphyrinic protonated core of the hybrid leads to the formation of self-assembled structures, so that the hybrids flocculate and their catalytic activity is fully suppressed. The low degree of chirality transfer observed for aqueous Michael and aldol reactions strongly suggests that these reactions take place under true "in water" organocatalytic conditions. The highly insoluble catalyst aggregates can easily be separated from the reaction products by centrifugation of the acidic reaction mixtures, and after neutralization and desalting, the sodium salts of the sulfonated amine-porphyrin hybrids, retaining their full catalytic activity, can be recovered in high yield.

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