Recent advancement in the area of asymmetric organocatalysis led to the development of new methodologies for the construction of valuable enantiopure molecules, including various heterocycles. As one of the latter class of compounds tetrahydropyrans (THPs) constitute a core structure of a wide array of bioactive natural products. A noticeable growth has been observed in the asymmetric synthesis of THPs using small organic molecules as catalysts. This Tutorial Review describes the organocatalytic methods available to furnish THPs as well as the application of these methodologies in the total synthesis of THP-based natural products.
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http://dx.doi.org/10.1039/c6cs00757k | DOI Listing |
Chem Asian J
January 2025
Jammu University: University of Jammu, Post-Graduate Department of Physics & Electronics, INDIA.
A simple method for constructing unsymmetrical 2-nitrobiaryls has been developed between substituted 1,4-dithiine-2-carbaldehyde and nitroolefins under metal-free conditions. To gain the advantage of the HOMO-raising effect of temporary substitutions on in situ generated dienamine intermediate, the present protocol established [4+2] benzannulation of 1,4-dithiane-tethered enals with nitroolefin. Further, easy unmasking of 1,4-dithiine units results in a benzannulation product like that of unsubstituted enals, which are difficult to access.
View Article and Find Full Text PDFOrg Lett
January 2025
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
Although methods for synthesizing chiral phosphorus scaffolds are available, the potential of this molecular chirality remains largely unexplored. Herein, we present a remote desymmetrization of prochiral biaryl phosphine oxides through an organocatalytic asymmetric arylation. This metal-free approach enables the efficient synthesis of a wide range of densely functionalized P(V)-stereogenic compounds with good to excellent yields and satisfactory enantioselectivities.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, Shihezi 832003, P. R. China.
An organocatalytic method for the SuFEx click reaction of gaseous SOF is described. Different organic bases such as DBU, TBD, triethylamine and Hünig's base can efficiently catalyze the SuFEx of SOF with various phenols to produce aryl fluorosulfates in 61-97% yields. Under the same conditions, pyridone, pyrazolone and amines can also react with SOF to afford the corresponding heteroaryl fluorosulfates or sulfamoyl fluorides in good yields.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) was used for the synthesis of cyclic imides via an amidation-cyclization-elimination cascade.
View Article and Find Full Text PDFBiomacromolecules
January 2025
Chair of Macromolecular Chemistry, Julius-Maximilians-Universität Würzburg, Röntgenring 11, 97070 Würzburg, Germany.
Postpolymerization modifications are valuable techniques for creating functional polymers that are challenging to synthesize directly. This study presents aliphatic polycarbonates with pendant thiol-reactive groups for disulfide formation with mercaptans. The reductive responsive nature of this reaction allows for reversible postpolymerization modifications on biodegradable scaffolds.
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