The palladium-catalyzed coupling of an aziridinylzinc chloride intermediate with alkenyl and aryl halides has been demonstrated. The method provides products with retention of aziridine stereochemistry. The utility of the coupling procedure is illustrated in the synthesis of structures related to l-furanomycin.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2996137 | PMC |
http://dx.doi.org/10.1021/ol101904a | DOI Listing |
Dalton Trans
January 2025
Institut für Anorganische Chemie. Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany.
Compared to aziridines, azaphosphiridines, which formally result from the replacement of a carbon atom by phosphorus, have been much less studied. In this work, accurate values for one of the most prominent properties, the ring strain energy (RSE), have been theoretically examined for a wide range of azaphosphiridine derivatives. Strongly related aspects of interest for developing the use of azaphosphiridines in heteroatom and polymer chemistry are ring opening reactions and polymerisations, the latter facilitated by their significantly high RSE.
View Article and Find Full Text PDFJACS Au
November 2024
Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.
We describe a metal-free aziridination of unactivated olefins to generate pyridinium aziridines. Subsequent cross-coupling affords -aryl aziridines, and reductive depyridylation affords N-H aziridines. Kinetics experiments, based on a variable time normalization analysis (VTNA), indicate that aziridination proceeds via a highly electrophilic -pyridinium iminoiodinane intermediate.
View Article and Find Full Text PDFThromb Res
January 2025
Jagiellonian University, Jagiellonian Centre for Experimental Therapeutics (JCET), Krakow, Poland. Electronic address:
Background: Protein disulfide isomerase 1 (PDIA1) and 3 (PDIA3) regulate platelet activation and thrombus formation. However, their role in the formation of platelet-derived extracellular vesicles (pEVs) remains unknown.
Aim: To characterise the effects of PDIA1 and PDIA3 inhibition on pEV formation in washed murine platelets in response to platelet glycoprotein VI (GPVI) receptor or intracellular calcium signal activation.
Angew Chem Int Ed Engl
January 2025
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Herein, we present the first catalytic asymmetric nucleophilic addition of diarylphosphines to 2H-azirines, facilitated by a chiral Mn(I) complex. This method not only provides access to novel class of derivatives of the aziridine core - a structural motif recognized for its antitumor and antibacterial properties - but also introduces a phosphine moiety alongside the generation of an NH moiety within a strained three-membered ring. The discovery of this new Mn(I) complex that both enables the reaction and induces stereoselectivity is pivotal, as it underscores the significant potential of this earth-abundant metal in advancing asymmetric catalysis.
View Article and Find Full Text PDFChem Commun (Camb)
October 2024
School of Pharmacy, Health Science Center, Xi'an Jiaotong University, 76 Yanta West Road, Xi'an, Shaanxi 710061, China.
We report a new TADF-catalyzed aziridination of alkenes under visible light. In this protocol, a free triplet nitrene is generated from the commercially available tosyl azide by energy transfer of the excited photocatalyst 4DPAIPN. Our finding enables the smooth installation of the strained aziridine ring into a remarkably wide scope of alkenes and pharmaceutical-derived olefins and natural products, as well as the synthesis of sitagliptin.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!