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Photoinduced stereoselective reactions using pyridinium salts as radical precursors.
Chem Commun (Camb)
January 2025
Department of Chemistry, Institute of Technology Delhi, Hauz Khas, New Delhi 110-016, India.
Pyridinium salts are amine surrogates that are abundant in nature and the redox active nature of the pyridinium salts allows them to serve as precursors for generating radical species under mild conditions that can be initiated by light, heat or metal catalysis. The stereoselective formation of products has always been a topic of interest for synthetic chemists worldwide. In this context, pyridinium salts can readily undergo single electron reduction to form a neutral radical, and the N-X bond's subsequent fragmentation furnishes the X radical without any harsh reaction conditions.
View Article and Find Full Text PDFEnantioselective Total Syntheses of Vallesamidine and Schizozygane Alkaloids.
J Am Chem Soc
January 2025
Department of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, Texas 75080, United States.
A general streamlined strategy for the enantioselective total syntheses of the schizozygane family of natural products and related alkaloid vallesamidine is described. Specifically, a catalytic enantioconvergent cross-coupling sets the quaternary stereogenic center in a pluripotent intermediate adorned with an olefin and three orthogonal carboxylate groups, upon which the modularity of the synthesis relies. A late-stage catalytic oxidative lactamization of an alkyne is instrumental in the first-generation synthesis of the schizozygane alkaloids.
View Article and Find Full Text PDFStereodivergent Construction of 3,3'-Disubstituted Oxindoles via One-Pot Sequential Allylation/Alkylation and Its Application to the Total Synthesis of Trigolute B and D.
J Am Chem Soc
January 2025
Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China.
The absolute and relative configurations of bioactive chiral molecules are typically relevant to their biological properties. It is thus highly important and desirable to construct all possible stereoisomers of a lead candidate or a given bioactive natural compound. Synergistic dual catalysis has been recognized as a reliable synthetic strategy for a variety of predictable stereodivergent transformations.
View Article and Find Full Text PDFAsymmetric Functionalization Harnessing Radical-Mediated Functional-Group Migration.
Angew Chem Int Ed Engl
January 2025
Shanghai Jiao Tong University, Frontiers Science Center for Transformative Molecules, 800 Dongchuan Road, 200240, Shanghai, CHINA.
Along with the renaissance of radical chemistry, the past decade has witnessed rapid development in radical-mediated rearrangement reactions. A wide diversity of radical approaches harnessing functional-group migration (FGM) have been devised to enhance both synthetic efficiency and molecular complexity. However, the application of FGM reactions to construct stereogenic centers remains underexplored owing to the inherent challenges of asymmetric radical reactions.
View Article and Find Full Text PDFCatalytic asymmetric photocycloaddition reactions mediated by enantioselective radical approaches.
Chem Soc Rev
January 2025
Pingyuan Laboratory, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, Henan, P. R. China.
The use of olefins in the construction of cyclic compounds represents a powerful strategy for advancing the pharmaceutical industry. Photocycloaddition has attracted significant interest from chemists due to its ability to exploit simple and readily available olefins along with their reaction patterns under mild conditions. Moreover, the sustainable and versatile pathways for generating highly reactive intermediates can greatly enrich both substrate diversity and reaction patterns.
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