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Amino Alcohol

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Introduction

Amino alcohols are a group of compounds that have both amino (-NH2) and  hydroxyl (-OH) groups. Amino alcohols are important structural elements that are frequently found in pharmaceutical agents and biologically active natural products. Within SciFinder®, more than 350,000 reactions are currently listed with amino alcohols with secondary alcohols and primary amines function as reactants take place. This fact indicates the diverse potential of these compounds in the chemical industry. Chiral amino alcohols are commonly used as drug intermediates and chiral ligands due to their good coordination ability of N and O atoms. They are widely used in medicine, chemical industry, materials and asymmetric synthesis.

Application

Medince: Cyclic amino alcohols form a large group of biologically active natural products; for example, quinine that is used for malaria treatment. One important class of cyclic amino alcohols is the polyhydroxylated alkaloids, also known as aza-sugars, e.g. castanospermine that was found to be a potent inhibitor of α- and β-glucosidases.

Intermediates: β-Amino alcohols are used as intermediates in the synthesis of a wide range of biologically active natural and synthetic products as well as in unnatural amino acids. The amino alcohols are generally derivatized to improve their chelating ability or to increase their steric directing effect and also used in asymmetric synthesis.

Chiral ligands: The β-amino alcohols also play an important role as chiral ligands, most commonly derived from natural sources. Chiral 1,2-amino alcohols are common structural motifs found in a vast array of natural and biologically active molecules.

Catalysts: Due to good coordination ability of nitrogen and oxygen atoms, amino alcohols can form complexes with many elements to generate chiral catalysts with excellent performance.

References:

  1. Vishal Srivastava, Pravin K. Singh, Sudhanshu Kanaujiac, Praveen P. Singh. Photoredox catalysed synthesis of amino alcohol. New Journal of Chemistry, 2018, 42(1): 688-691.
  2. Torsten Sehl, Zaira Maugeri, Dörte Rother. Multi-step synthesis strategies towards 1,2-amino alcohols with special emphasis on phenylpropanolamines. Journal of Molecular Catalysis B: Enzymatic, 2015, 114: 65-71.

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