We disclose herein a chiral phosphoric-acid-catalyzed enantioselective addition reaction of alcohols to fluoroalkylated biaryl 1,3-oxoazepines, which furnished a wide range of bridged biaryls bearing a fluoroalkylated quaternary carbon stereocenter on the seven-membered ring in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee). Our method can be used for the modification of several natural products and bioactive molecules. Preliminary studies revealed that the products obtained in this reaction exhibit good in vitro bioactivities against two plant pathogens.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.4c04813 | DOI Listing |
Org Lett
January 2025
Key Laboratory of Chemical Biology and Traditional Chinese Medicine (Ministry of Educational of China), Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China.
We disclose herein a chiral phosphoric-acid-catalyzed enantioselective addition reaction of alcohols to fluoroalkylated biaryl 1,3-oxoazepines, which furnished a wide range of bridged biaryls bearing a fluoroalkylated quaternary carbon stereocenter on the seven-membered ring in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee). Our method can be used for the modification of several natural products and bioactive molecules. Preliminary studies revealed that the products obtained in this reaction exhibit good in vitro bioactivities against two plant pathogens.
View Article and Find Full Text PDFACS Bio Med Chem Au
December 2024
Department of Chemistry, The University of Hong Kong, 999077 Hong Kong Special Administrative Region, Hong Kong, China.
Macrocyclization is a vital process in the biosynthesis of ribosomally synthesized and post-translationally modified peptides (RiPPs), significantly enhancing their structural diversity and biological activity. Universally found in living organisms, cytochrome P450 enzymes (P450s) are versatile catalysts that facilitate a wide array of chemical transformations and have recently been discovered to contribute to the expansion and complexity of the chemical spectrum of RiPPs. Particularly, P450-catalyzed biaryl-bridged RiPPs, characterized by highly modified structures, represent an intriguing but underexplored class of natural products, as demonstrated by the recent discovery of tryptorubin A, biarylitide and cittilin.
View Article and Find Full Text PDFJ Org Chem
December 2024
Université de Bourgogne, UFR des Sciences et Techniques, ICMUB UMR-CNRS 6302, BP 47870, 21078 Dijon Cedex, France.
Chiral diphosphines with a biphenyl bridge and the chirality borne by the phosphorus atoms and not due to the atropoisomery of the biaryl backbone have been scarcely studied. Herein, we report the asymmetric synthesis of the (,)-2,2'-bis(ferrocenylphenylphosphino)biphenyl (BipheP*) ligand and its application in Rh-catalyzed hydrogenation. The synthesis was based on the enantioselective preparation of P-chirogenic ferrocenyl(-bromophenyl)phenylphosphine by the reaction of -phosphine-borane with 1,2-dibromobenzene and its homocoupling into BipheP*.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai, 400076, India.
The directing group (DG)-assisted approach has so far been the major route to achieve selective C-H activation at both proximal and distal positions. While rhodium catalysts are highly effective in DG-assisted ortho-C-H arylation, meta-C-H arylation with rhodium has not yet been reported. In this study, we present the first example of Rh-catalyzed meta-C-H arylation of arenes.
View Article and Find Full Text PDFSmall
November 2024
State Key Laboratory of Electrical Insulation and Power Equipment, Xi'an Jiaotong University, Xi'an, 710049, China.
The escalating demand for high-power and compact-size advanced electronic devices and power systems necessitates polymers to exhibit superior electrical properties even under harsh environments. However, reconciling the seemingly contradictory attributes of excellent electrical properties and thermal stability poses a formidable challenge for current epoxy polymer (EP) materials and their applications. To meet the need, here two classes of bi-aryl diamine curing agents are described that enable polymers to exhibit well-balanced thermal and dielectric properties with functional bridging groups.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!