N-acylation of ethanolamine using lipase: a chemoselective catalyst

Abstract

SummaryThe N-acylation of ethanolamine (2) with various fatty acids 1a–d and esters of fatty acids 1e–h using Candida antarctica B lipase (Novozym® 435) are described and optimum conditions for selective N-acylation rather than O-acylation are also discussed. Microwave assisted solution phase, solid supported and conventional methods were investigated and results were compared. There is a synergy between the enzyme catalysis and microwave irradiation.

Continuous Flow Aerobic Alcohol Oxidation Reactions Using a Heterogeneous Ru(OH)x/Al2O3 Catalyst

“…Conversion of alcohols to carbonyl compounds is one of the most common transformations in organic chemistry. Process-scale alcohol oxidations are often done using stoichiometric or catalytic reagents, such as pyridine·SO 3 1 − 3 and NaOCl/TEMPO (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxyl); 4 − 7 however, there has been long-standing interest in the development of aerobic methods that generate essentially no byproducts. Applications of aerobic alcohol oxidation in the pharmaceutical and fine-chemical industries have been limited, often because the performance of existing catalytic methods does not match or exceed that of traditional oxidation methods and/or because mixtures of oxygen gas and organic solvents represent a potential safety hazard.…”

Study of the Influence of Microwave and Conventional Heating on the Lipase-Catalyzed Esterification of Lauric Acid with Different Alcohols

“…The effects of reaction temperature can be attributed to its effect on substrate solubility as well as to its direct influence on the reaction and the enzyme [13]. Higher reaction temperatures also promote collisions between substrate and the enzyme resulting in accelerated reaction rates [14].…”

“…Since lipase-catalyzed reactions are rather sluggish in nature, the synergism with microwave can be expected to enhance the reaction rates. Such an exploration has been tried out earlier to witness rate enhancement in microwave irradiated lipasecatalyzed reactions [14].…”

Metal‐Free O‐Selective Direct Acylation of Amino Alcohols Through Pseudo‐Intramolecular Process

“…Selective N ‐acylation of amino alcohols was performed by using lipase and dibutyltin oxide as a catalyst, and both methods were conducted under microwave irradiation. N ‐Acylation of α,β‐diamino alcohol was also reported .…”