Multifunctional “Click” Prolinamides: A New Platform for Asymmetric Aldol Reactions in the Presence of Water with Catalyst Recycling

Abstract

Click" chemistry is combined with organocatalysis to fabricate a multifunctional C 3 -symmetrical dendritic prolinamide with a hydrophobic aromatic core and hydrophilic triazolinium arms that exhibit high efficiency in catalyzing the asymmetric aldol reaction with cyclic ketones. The catalyst is water-compatible and remains active for five consecutive catalytic runs with a low catalyst loading (2 mol%), yielding the aldol products in high yields, diastereo-and enantioselectivities.

Preparation of Immobilized L‐Prolinamide Via Enzymatic Polymerization of Phenolic L‐Prolinamide and Evaluation of Its Catalytic Performance for Direct Asymmetric Aldol Reaction

“…In the present research, we chose phenolic L-prolinamide, while the prolinamide was considered as an active and highly stereoselective catalyst for the direct aldol reaction in the presence of water, [34][35][36][37][38][39] as a monomer to synthesize polymer-supported L-prolinamide via the enzymatic polymerization catalyzed by horseradish peroxidase (HRP). 40,41 Such an approach is facile and competitive.…”

A Magnetoclick Imidazolidinone Nanocatalyst for Asymmetric 1,3‐Dipolar Cycloadditions

“…In the course of our investigations into applications of MacMillans imidazolidinone-based catalyst, [15] the design of a multifunctional prolinamide using "click chemistry" [16] and a recyclable magnetic nanocatalyst, [17] we became interested to design a novel magnetically recoverable imidazolidinone catalyst using the azide-alkyne cycloaddition. The MNPs supported imidazolidinone catalyst has been prepared via two strategies using "click chemistry" [18] as shown in Scheme 2.…”

Application of Polyamines and Amino Acid Derivatives Based on 2-Azabicycloalkane Backbone in Enantioselective Aldol Reaction

“…Nowadays, the use of water as an environmentally friendly reaction medium is highly recommended. Since proline is not effective in aqueous media, prolinamide derivatives were developed as highly reactive and stereoselective catalysts in either water or brine with a notably low catalyst load [ 25 , 26 , 27 , 28 , 29 ]. In our experiments, the aldol reaction was performed in brine at room temperature, in the presence of acetic acid (20 mol%) as a co-catalyst.…”