The vicinal amino alcohol is a common motif in natural products and pharmaceuticals. Amino acids constitute a natural, inexpensive, and enantiopure choice of starting material for the synthesis of such functionalities. However, the matters concerning diastereoselectivity are not obvious. This Perspective takes a look in the field of diastereoselective synthesis of vicinal amino alcohols starting from amino acids using various methods.
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http://dx.doi.org/10.1039/c2ob25357g | DOI Listing |
Org Biomol Chem
January 2025
Ural Federal University named after the First President of Russia B.N. Eltsin, Mira st. 19, Yekaterinburg, 620002, Russian Federation.
A multi-component method for the synthesis of pyrimido[5,4-]azolo[1,5-]pyrimidines and pyrimido[4,5-][1,2,4]triazolo[5,1-][1,2,4]triazines has been developed. It was shown that vicinal amino-nitrile and amino-ethoxycarbonyl derivatives of azolo[1,5-]pyrimidines and azolo[5,1-][1,2,4]triazines were converted to tricyclic heterocycles in the "AcOH-RC(OEt)-amine" system. Reaction conditions were optimized, patterns of this process were investigated, and intermediates were isolated.
View Article and Find Full Text PDFChem Asian J
January 2025
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan.
Herein, we report the radical azidoamination of styrenes via the use of a combination of sodium azide and (diphenylmethylene)amino benziodoxolone under visible-light irradiation. This approach to unsymmetrical diamination provides a simple and practical method for constructing vicinal diamine scaffolds with two distinct and easily modifiable amino functionalities.
View Article and Find Full Text PDFJ Org Chem
January 2025
International Joint Research Center for Molecular Science, College of Chemistry and Environmental Engineering, College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen, Guangdong 518060, P. R. China.
We disclosed a new strategy for the synthesis of 1,2-amino alcohols enabled by visible light without the requirement of a photocatalyst and metal. Under light irradiation at 400 nm, the reaction of carbonyl derivatives and -arylamines proceeds via an electron-donor-acceptor (EDA) intermediate, obtaining diverse vicinal amino alcohols decorated with a two-electron-rich/-deficient aryl group.
View Article and Find Full Text PDFMolecules
November 2024
Departamento de Química Orgánica e Inorgánica, Facultad de Ciencias, and Instituto del Agua, Cambio Climático y Sostenibilidad (IACYS)-Unidad de Química Verde y Desarrollo Sostenible, Universidad de Extremadura, 06006 Badajoz, Spain.
This publication reports a facile and convenient preparation of tri--acetyl-glucopyranoses, derived from the corresponding 2-deoxyaminosugar, where the vicinal anomeric and C2 positions are decorated by azido and (thio)ureido groups, respectively. This double functionalization leads to an inherently chiral core incorporating the versatile azido and (thio)ureido linkages prone to further manipulation. The latter also provides a structural element for hydrogen-bonded donor-acceptor (HB-DA) sites, which are of immense value in organocatalytic pursuits.
View Article and Find Full Text PDFNat Commun
November 2024
College of Chemistry, Zhengzhou University, Zhengzhou, 450001, China.
Enantioenriched unsymmetrical vicinal diamines are important basic structural motifs. While catalytic asymmetric intermolecular 1,2-diamination of carbon-carbon double bonds represents the most straightforward approach for preparing enantioenriched vicinal-diamine-containing heterocycles, these reactions are often limited to the installation of undifferentiated amino functionalities through metal catalysis and/or the use of stoichiometric amounts of oxidants. Here, we report organocatalytic enantioselective unsymmetrical 1,2-diaminations based on the rational design of a bifunctional 1,2-diamination reagent, namely, azocarboxamides (ACAs).
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