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Stereospecific Radical Bromination of β-Aryl Alcohols with Thiourea Additives Through A Serendipitous Discovery of A 1,2-Aryl Migration.
Chemistry
January 2025
Department of Natural Sciences, The Open University of Israel, Ra'anana 4353701, Israel.
The development of new protocols for stereospecific and stereoselective halogenation transformations by mild reaction conditions is a highly desirable research target for the chemical and pharmaceutical industries. Following the straightforward methodology for directly transforming a wide scope of alcohols to alkyl bromides and chlorides using substoichiometric amounts of thioureas and N-halo succinimides (NXS) as a halogen source in a single step, we noticed that in apolar solvents bromination of chiral secondary alcohols did not produce the expected racemates. In this study, the stereochemical aspects of the bromination reaction were examined.
View Article and Find Full Text PDFRapid Synthesis of the Spiroketal Subunit of Neaumycin B: Stereochemical Aspects of Singly Anomeric Spiroketals and Proposal for a Stereocenter Reassignment.
Org Lett
December 2024
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
Neaumycin B is a complex polyketide that shows phenomenal cytotoxicity against U87 glioblastoma cells. The singly anomeric spiroketal core is a notable subunit in the natural product's structure. We report a rapid and convergent approach to the spiroketal group, resulting in the formation of two isomeric singly anomeric spiroketals.
View Article and Find Full Text PDFCatalytic kinetic resolution of helical polycyclic phenols via an organocatalyzed enantioselective dearomative amination reaction.
Sci Adv
November 2024
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, China.
Despite the considerable potential applications for helically chiral molecules across various sectors, their catalytic asymmetric synthesis remains nascent and has seen very limited advancement compared to that of central and axial chiral compounds, primarily owing to the scarcity of available starting materials and the immense challenges associated with achieving stereochemical control. Herein, we report an innovative approach to the facile synthesis and catalytic kinetic resolution of uniquely structured and stereochemically complex helical polycyclic phenols by using a steric hindrance-regulated enantioselective dearomative amination reaction. The distinguished aspects of this method include the exceptional stability of the dearomatized products and impressive versatility of the recovered substrates in the construction of enantioenriched helical frameworks.
View Article and Find Full Text PDFMechanism and stereoselectivity in metal and enzyme catalyzed carbene insertion into X-H and C(sp)-H bonds.
Chem Soc Rev
November 2024
Department of Organic Chemistry, Indian Institute of Science, Bengaluru-560012, Karnataka, India.
Constructing highly proficient C-X (X = O, N, S, ) and C-C bonds by leveraging TMs (transition metals) (Fe, Cu, Pd, Rh, Au, ) and enzymes to catalyze carbene insertion into X-H/C(sp)-H is a highly versatile strategy. This is primarily achieved through the generation of metal carbenes from the interaction of TMs with diazo compounds. Over the last few decades, significant advancements have been made, encompassing a wide array of X-H bond insertions using various TMs.
View Article and Find Full Text PDFStructural basis for adhesin secretion by the outer-membrane usher in type 1 pili.
Proc Natl Acad Sci U S A
October 2024
Department of Cell Biology and Physiology, Washington University School of Medicine, Saint Louis, MO 63110.
Gram-negative bacteria produce chaperone-usher pathway pili, which are extracellular protein fibers tipped with an adhesive protein that binds to a receptor with stereochemical specificity to determine host and tissue tropism. The outer-membrane usher protein, together with a periplasmic chaperone, assembles thousands of pilin subunits into a highly ordered pilus fiber. The tip adhesin in complex with its cognate chaperone activates the usher to allow extrusion across the outer membrane.
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