Ring-Opening of Epoxides with Amines for Synthesis of β-Amino Alcohols in a Continuous-Flow Biocatalysis System

Abstract

An efficient method for the preparation of β-amino alcohols catalyzed by lipase TL IM from Thermomyces lanuginosus in a continuous-flow reactor was developed. The eco-friendly biocatalyst combined with continuous-flow reaction technology displayed high efficiency in the synthesis of β-amino alcohols. The benign reaction conditions (35 °C) and short residence time (20 min), together with the use of low cost and readily available starting materials, make this synthetic approach a promising alternative to current β-amino alcohol synthesis.

Click Chemistry: Reaction Rates and Their Suitability for Biomedical Applications

“…1,44 Epoxide reactions are crucial in organic synthesis due to the high reactivity of the oxygen-containing three-membered ring to synthesize structural polymers. 45 The reactivity stems from the polarity and angle strain, facilitating interactions with various Lewis acids and nucleophilic reactants, such as amines, alcohols, and thiols, to form β-amino alcohols, 46 β-hydroxyl alcohols, and β-hydroxy sulfides, respectively. 47 Among these, β-amino alcohols serve as vital building blocks for biologically active products including antihypertensive drugs.…”

Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane

“…Various methodologies were suggested for their synthesis. − The classical pathway for the synthesis of phenethylamines is the reduction of β-nitrostyrenes (Scheme a) or benzylcyanides . Other synthetic approaches include ring-opening of aryloxiranes with arylamines, nickel-catalyzed alkylative ring-opening of 2-arylaziridines or nickel-photoredox coupling of aryl iodides and aziridines (Scheme b) or copper-catalyzed ring opening of 2-arylaziridines with alcohols, metal- and photocatalyzed hydro- or carboamination of alkenes and alkynes (Scheme c), hydroxyamination of styrenes, reductive amination, as well as alkylation of amines with alkyl halides . Considering that the majority of naturally occurring and synthetic derivatives of phenethylamine 3 (Figure ) ,,, possess an N -methyl group, some of these methods require an additional alkylation step .…”

Synthesis of β-amino alcohols by ring opening of epoxides with amines catalyzed by sulfated tin oxide under mild and solvent-free conditions

“…16 Better techniques have recently been discovered for this transformation. [17][18][19][20][21][22][23][24][25][26] These protocols do have certain drawbacks, though, like lengthy reaction times, high temperatures, poor regioselectivity, moderate yields, the need for stoichiometric amounts of catalyst and reagent, the possibility of allylic alcohol rearrangement, the potential dangers associated with handling moisture-sensitive reagents during catalyst preparation, and the fact that they are typically limited to aromatic amines.…”