Shake it up baby! Simply shaking a polymer-supported reagent and the racemic amine at room temperature kinetically resolves a broad range of N-heterocycles with good selectivity. The polymer-supported reagents are robust, easy to regenerate, and can be reused dozens of times. Cleavable acyl groups can be used to give access to both amine enantiomers in a single resolution.
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http://dx.doi.org/10.1002/anie.201204991 | DOI Listing |
Polymers (Basel)
April 2023
Department of Chemistry and Biochemistry, Hope College, Holland, MI 49422, USA.
Biodegradable polymers are desirable to mitigate the environmental impact of plastic waste in the environment. Over the past several decades, the development of organocatalytic ring-opening polymerization (OROP) has made the synthesis of many new types of biodegradable polymers possible. In this research article, the first example of an oxygen atom transfer reagent pendant on a biodegradable polymer backbone is reported.
View Article and Find Full Text PDFFront Chem
August 2022
Laboratorio de Química Farmacéutica (DQO), Facultad de Química, Universidad de la República, Montevideo, Uruguay.
The reversibility of the thiol-thioester linkage has been broadly employed in many fields of biochemistry (lipid synthesis) and chemistry (dynamic combinatorial chemistry and material science). When the transthioesterification is followed by a S-to-N acyl transfer to give an amide bond, it is called Native Chemical Ligation (NCL), a high-yield chemoselective process used for peptide synthesis. Recently, we described thioglycolic acid (TGA) as a useful reagent for thioester deprotection both in solution and anchored to a solid-support under mild conditions.
View Article and Find Full Text PDFACS Chem Neurosci
April 2022
Department of Chemistry, Columbia University, New York, New York 10027, United States.
Optical imaging of changes in the membrane potential of living cells can be achieved by means of fluorescent voltage-sensitive dyes (VSDs). A particularly challenging task is to efficiently deliver these highly lipophilic probes to specific neuronal subpopulations in brain tissue. We have tackled this task by designing a solubilizing, hydrophilic polymer platform that carries a high-affinity ligand for a membrane protein marker of interest and a fluorescent VSD.
View Article and Find Full Text PDFTetrahedron
August 2021
Laboratorio de Química Farmacéutica, (DQO), Facultad de Química, Universidad de la República, Gral.Flores 2124, Montevideo, CP 11800, Uruguay.
Classic acetyl thioester protection/deprotection methodologies are widely used in organic synthesis, but deprotection step usually requires harsh conditions not suitable for labile substrates. In this work, a new method for thioester deprotection using a thiotransesterification approach is described. Firstly, thioglycolic acid (TGA) was identified as a good deprotecting reagent in solution.
View Article and Find Full Text PDFOrg Biomol Chem
July 2021
School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK.
A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamides via stable diazonium salts, prepared using a polymer-supported nitrite reagent and p-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets.
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