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Ruthenium-Catalyzed Remote Trifunctionalization of Non-Activated Alkenes via Cyano Migration and -C(sp)-H Functionalization.
Org Lett
January 2025
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, People's Republic of China.
A novel Ru-catalyzed radical-triggered trifunctionalization of hexenenitriles is presented, employing a strategy of remote cyano group migration and -C(sp)-H functionalization. Through remote cyano migration, the alkenyl moiety undergoes difunctionalization to the formation of a benzylic radical intermediate. This intermediate facilitates -selective C-H bond addition relative to the C-Ru bond within the Ru(III) complex, ultimately enabling trifunctionalization.
View Article and Find Full Text PDFVisible-light-promoted cascade cyclization of -arylacrylamides with bromomethyl sulfone: access to sulfonylmethylated phenanthridines.
Org Biomol Chem
January 2025
Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450052, China.
We present a visible-light-promoted radical cascade cyclization reaction sulfonylmethylation, cyano insertion, and radical cyclization of unactivated alkenes bearing cyano groups. This strategy enables the rapid synthesis of sulfonylmethylated phenanthridines under mild conditions with broad substrate compatibility, operational simplicity, and mild reaction conditions. The developed approach provides a novel pathway for assembling complex polycyclic nitrogen-containing frameworks, addressing a critical synthetic challenge and expanding the toolbox of photochemical transformations in organic synthesis.
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 PDFUnveiling astaxanthin: biotechnological advances, delivery systems and versatile applications in nutraceuticals and cosmetics.
Arch Microbiol
January 2025
School of Bio Sciences and Technology, Vellore Institute of Technology, Vellore, 632014, India.
Astaxanthin (ASX), "king of carotenoids", is a xanthophyll carotenoid that is characterized by a distinct reddish-orange hue, procured from diverse sources including plants, microalgae, fungi, yeast, and lichens. It exhibits potent antioxidant and anti-ageing properties and has been demonstrated to mitigate ultraviolet-induced cellular and DNA damage, enhance immune system function, and improve cardiovascular diseases. Despite its broad utilization across nutraceutical, cosmetic, aquaculture, and pharmaceutical sectors, the large-scale production and application of ASX are constrained by the limited availability of natural sources, low production yields and stringent production requirements.
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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