2-Hydroxymethyl-18-crown-6 as an efficient organocatalyst for αaminophosphonates synthesized under eco-friendly conditions, DFT, molecular docking and ADME/T studies.

Eco-friendly and simple procedure has been developed for the synthesis of αaminophosphonates that act as topoisomerase II α-inhibiting anticancer agent, using 2-hydroxymethyl-18-crown-6 as an unexpected homogeneous organocatalyst in multicomponents reaction of aromatic aldehyde, aniline and diethylphosphite in one pot reaction. This efficient method proceeds with catalytic amount, transition metal-free, at room temperature within short reaction time, giving the αaminophosphonates derivatives in high chemical yields (up to 80%). Theoretical DFT calculations of three compounds and were carried out in a gas phase at CAM-B3LYP 6-31G (d,p) basis set to predict the molecular geometries and chemical reactivity descriptors.

Enantioselective bio-deacylation of arylalkyl acetates using tertiary amines as additive under promiscuous conditions.

Herein, we describe the impact of the introduction of tertiary amines as additive during the enzymatic kinetic resolution via deacylation of some arylalkyl acetates 1a-8a under promiscuous conditions. Two CAL-B preparations were examined: Novozym®435 and CHIRAZYME® L-2, c.-f.

Access to valuable building blocks by the regio- and enantioselective ring opening of itaconic anhydride by lipase catalysis.

Herein, we report for the first time the highly regio- and enantioselective ring opening of a biobased itaconic anhydride catalyzed by the lipase () in -butyl methyl ether (TBME) at room temperature. This method is easy, efficient and eco-friendly and can be performed in one step with a series of highly valuable monoester itaconates (achiral or enantioenriched) using various alcohols as nucleophiles with 100% atom economy. In all cases, the β-monoester isomer was the predominant product of the reaction.

Efficient access to both enantiomers of 3-(1-hydroxyethyl)phenol by regioselective and enantioselective CAL-B-catalyzed hydrolysis of diacetate in organic media by sodium carbonate.

In the present paper, we describe several pathways employing immobilized lipase from Candida antarctica B (CAL-B) as biocatalyst to prepare easily both enantiomers of 3-(1-hydroxyethyl)phenol. We have applied hydrolysis with Na CO in organic media under mild conditions. The reaction parameters solvent effect, amount of lipase, and Na CO were examined with 3-(1-acetoxyethyl)phenyl acetate as substrate.

CAL-B-Catalyzed deacylation of benzylic acetates: Effect of amines addition. Comparison of several approaches.

Herein, we report an efficient enantioselective cleavage of the acyl-moity of some secondary benzylic acetate derivatives catalyzed by lipase B from Candida antarctica (CAL-B) in the presence of triethylamine, as additive, in non aqueous media. The influence of the hydrophobicity of two solvent, the basicity of three amines and the amount of CAL-B were studied in the presence/absence of molecular sieves 4Å. The best results in term of selectivity are achieved using the triethylamine as basic additive and in that case, the reactivity is only best at low conversion.