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Unlocking the catalytic precision of ligand-controlled enzymatic halogenation.
Proc Natl Acad Sci U S A
January 2025
School of Biomolecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology (VISTEC), Rayong 10120, Thailand.
A single-component flavin-dependent halogenase, AetF, has emerged as an attractive biocatalyst for catalyzing halogenation. However, its flavin chemistry remains unexplored and cannot be predicted due to its uniqueness in sequence and structure compared to other flavin-dependent monooxygenases. Here, we investigated the flavin reactions of AetF using transient kinetics.
View Article and Find Full Text PDFOrganocatalytic Asymmetric Construction and Application of Axially Chiral Spiro-bisindoles.
Angew Chem Int Ed Engl
December 2024
Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, China.
Spiro skeletons have emerged as a privileged class of chiral carriers across various research fields, including asymmetric catalysis and functional materials, due to their remarkable configurational rigidity. However, limited structural diversity of spiro frameworks significantly restricts the expansion of their applications. Here we present a new class of axially chiral spiro-bisindole frameworks and report their first enantioselective construction via a chiral phosphoric acid-catalyzed intramolecular dehydrative cyclization reaction.
View Article and Find Full Text PDFEnantioselective Synthesis of Atropisomeric Tri-Axis Naphthalenes via Diels-Alder Reaction and Dehydrative Aromatization of Isobenzofurans.
Angew Chem Int Ed Engl
December 2024
Department of Chemistry, Fudan University, 220 Handan Rd., Shanghai, 200433, China.
Atropisomers with multiple stereogenic axes have attracted much attention due to their increasing significance in the fields of natural products, chiral materials, and drug discoveries. However, the catalytic stereoselective construction of axially chiral ring scaffolds with more than two axes on a single benzene ring remains a challenging task. Herein, we present an efficient method for synthesizing triaxially chiral polysubstituted naphthalene scaffolds via sequential Ni(II)-catalyzed Diels-Alder reaction of isobenzofurans and TfOH-promoted dehydrative aromatization reaction.
View Article and Find Full Text PDFPhotocatalyzed Dehydration of 1-Aryl-1,2-Ethanediols to Methyl Ketones Driven by Eosin Y Fragmentation Products.
Chemistry
December 2024
Department of Chemistry and Pharmacy, University of Regensburg, Universitätstr. 31, 93053, Regensburg, Germany.
Herein, we report a mild photocatalytic redox-neutral dehydration of aryl-1,2-ethanediols forming the respective methyl ketones. In the proposed mechanistic cycle an initial hydrogen atom abstraction (HAT) is followed by a 1,2-spin center shift (SCS) as key steps. Interestingly, Eosin Y was found to act as a pre-catalyst dissociating into a catalytically active mixture under irradiation.
View Article and Find Full Text PDFUrazoles as Heterocyclic Directing Groups in Ru(II)-Catalyzed Annulation of N-H/C-H Bonds with Vinylene Carbonate.
J Org Chem
December 2024
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
The development of novel directing groups is a valuable strategy to secure the advancement of catalytic C-H functionalization. To illustrate the feasibility of urazoles as heterocyclic directing groups, we herein present the ruthenium(II)-catalyzed annulation of N-H/C-H bonds on -aryl urazoles with vinylene carbonate. This transformation provides the rapid construction of triazolocinnoline derivatives as hemiaminal and dehydrated forms.
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