Kinetic resolution of racemic planar-chiral vinylcymantrenes by molybdenum-catalyzed asymmetric metathesis dimerization

• Haruna Imazu,
• Hitoshi Izu,
• Yasuhiro Ohki and
• Masamichi Ogasawara

Beilstein J. Org. Chem. 2026, 22, 568–574, doi:10.3762/bjoc.22.42

• resolution; molybdenum; olefin metathesis; planar chirality; Introduction The development of the well-defined molybdenum- [1][2] or ruthenium-alkylidene [3][4][5] catalysts has proven the olefin metathesis reaction to be a powerful tool in organic synthesis. Asymmetric extension is a recent trend in

Molecular tweezer–peptide conjugates disrupt the protein–protein interaction between survivin and histone H3 essential in mitosis

• Catherine Gsell,
• Philipp Rebmann,
• Karina Opara,
• Christine Beuck,
• Peter Bayer,
• David Bier,
• Ingrid R. Vetter and
• Thomas Schrader

Beilstein J. Org. Chem. 2026, 22, 557–567, doi:10.3762/bjoc.22.41

• + ions that were surprisingly observed in the center of the aromatic ring structure, perhaps due to their weaker binding of the hydrate shell. However, this early crystal structure was obtained with the diacetoxytweezer in organic solution [18]. Interestingly, a similar unexpected inclusion of a

Experimental and DFT studies on the regioselective methanolysis of 5-azido-9-oxabicyclo[6.1.0]nonan-4-yl 4-nitrobenzoate isomers

• İlknur Polat,
• Selçuk Eşsiz and
• Emine Salamci

Beilstein J. Org. Chem. 2026, 22, 547–556, doi:10.3762/bjoc.22.40

• process, highlighting its precision and efficiency. Keywords: azides; 8-azidocyclooct-4-en-1-yl 4-nitrobenzoate; DFT; epoxycyclooctane azide; methanolysis; Introduction Organic azides are very important precursors for the preparation and synthesis of various nitrogen-containing compounds, as well as

• NaHCO3 (0.78 g, 9.29 mmol) were added to the solution and stirred for 1.5 hours. Subsequently, 50 mL of 1.5 M NaOH solution was added and the reaction mixture was stirred for 15 min at 0 °C, then extracted with dichloromethane (4 × 30 mL). The organic layer was dried over Na2SO4, filtered, and evaporated

• . The progress was monitored by TLC and the reaction was completed in 36 hours. The solvent was removed by rotary evaporation, 30 mL water was added to the residue and the mixture was extracted with ethyl acetate (4 × 25 mL). The combined organic phases were dried over Na2SO4 and concentrated in vacuo

Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B

• Horst Weber,
• Kim-Thao Tran-Cong,
• Bernhard Mayer,
• Guido J. Reiss,
• Iryna S. Konovalova,
• Marc S. Appelhans,
• Kenneth R. Wood and
• Claus M. Passreiter

Beilstein J. Org. Chem. 2026, 22, 535–546, doi:10.3762/bjoc.22.39

• Biotechnology, Heinrich-Heine-University Duesseldorf, 40225 Duesseldorf, Germany Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Duesseldorf, 40225, Duesseldorf, Germany Institute of Inorganic Chemistry and Structural Chemistry, Heinrich-Heine-University Duesseldorf, 40225

• . Successive extraction with 0.1 N NaOH (5 × 20 mL) afforded a clear alkaline water phase that was acidified with dilute sulfuric acid and extracted with diethyl ether (5 × 20 mL). The organic phase was washed with water, dried over MgSO4, filtered and evaporated under reduced pressure to give 3,1 g (51.2%) of

• ) and extracted with diethyl ether (3 × 20 mL). The remaining aqueous layer was acidified using 0.1 N H2SO4 and extracted with diethyl ether (3 × 30 mL). The organic phase was washed with NaHCO3 solution (1%) and water, dried with MgSO4, filtered and evaporated to give 520 mg (57%) of 6 (CAS: 66050-33-7

Get a better glimpse on sequential photoreactions of trisnorbornadienes with ¹⁹F NMR spectroscopy

• Julian Felix Maria Hebborn,
• Ben Eric Merten,
• Thomas Paululat and
• Heiko Ihmels

Beilstein J. Org. Chem. 2026, 22, 527–534, doi:10.3762/bjoc.22.38

• ]heptadien-2-yl)-1,3,2-dioxaborolane (1e, 501 mg, 2.30 mmol), Pd(PPh3)4 (66.5 mg, 57.5 µmol, 5 mol %), THF (5.0 mL), and aq. NaOH (5.7 mmol, 2.7 M, 2.1 mL) was stirred at 80 °C for 16 h under anaerobic conditions [22]. After cooling the emulsion to room temperature, EtOAc (15 mL) was added and the organic

Synthesis and uranyl(VI) extraction performance of a calix[4]pyrrole–tetrahydroxamic acid receptor

• Sara Karnib,
• Rana Baydoun,
• Wissam Zaidan,
• Nancy AlHaddad,
• Omar El Samad,
• Bilal Nsouli,
• Francine Cazier-Dennin and
• Pierre-Edouard Danjou

Beilstein J. Org. Chem. 2026, 22, 486–494, doi:10.3762/bjoc.22.36

• receptors bearing both anion- and cation-binding sites, as well as systems capable of promoting ion-pair formation [23][24]. As effective chelating agents for a broad range of transition metals, hydroxamic acids constitute an important class of organic compounds that have attracted considerable attention

• corresponding hydroxamic acid, with no detectable acid-derived by-products. Solubility tests revealed that PCP HA is soluble exclusively in highly polar aprotic solvents (DMSO, DMF) and remains completely insoluble in other common organic solvents (chloroform, ether, etc.) and water. The absence of ligand

Recent advances in the stereoselective synthesis of distal biaxially chiral molecules

• Fanxing Zhou,
• Chen Zhang,
• Lingyu Sun,
• Yiyun Fang,
• Siming Zheng,
• Lina Hu,
• Mengyang Shen,
• Zhen Zhao,
• Wei Xu,
• Yunqiang Sun and
• Zi-Qiang Rong

Beilstein J. Org. Chem. 2026, 22, 461–479, doi:10.3762/bjoc.22.34

• chiral scaffolds, which arise from hindered rotation between two planes connected by a single bond, have attracted increasing attention due to their widespread applications in chiral ligands, organocatalysts [1], and functional materials [2], making them highly valuable molecular frameworks in organic

• prospects in the field of chiral organic material design. In 2025, Hong and co-workers successfully predicted a series of novel Sadphos (sulfinamide phosphine) ligands and accomplished the first enantioselective Ni-catalyzed Suzuki–Miyaura cross-coupling reaction (Scheme 24) [63]. Their work validated the

Structural reassignment of compound 968, an allosteric glutaminase inhibitor

• Lindsey A. Albertelli,
• Sainabou Jallow,
• Chun Li and
• Scott M. Ulrich

Beilstein J. Org. Chem. 2026, 22, 455–460, doi:10.3762/bjoc.22.33

• EtOAc (70 mL), which was separated and washed with water (3 × 50 mL). The organic layer was dried with anhydrous MgSO4, filtered, and the solvent removed by rotary evaporation to yield 3-bromo-4-dimethylaminobenzaldehyde as a thick gold oil (5.49 g, 89%). 1H NMR (400 MHz, CDCl3) δ 9.78 (s, 1H), 8.01 (m

Concept-driven strategies in target-oriented synthesis

• David Yu-Kai Chen,
• Chao Li and
• Yefeng Tang

Beilstein J. Org. Chem. 2026, 22, 451–454, doi:10.3762/bjoc.22.32

• National Institute of Biological Sciences, 7 Science Park Road ZGC Life Science Park, Beijing,102206, China School of Pharmaceutical Sciences, Tsinghua University, 100084 Beijing, China 10.3762/bjoc.22.32 Humankind’s fascination with organic molecules and their functions holds a special place in the

• history of science. Indeed, organic compounds have an unparalleled track record in elucidating the mysteries behind a wide range of physical, chemical, and biological phenomena, and advances in chemical synthesis have been instrumental in these explorations. Specifically, target-oriented syntheses of

• complex organic architectures have witnessed remarkable achievements in recent years, continuously redefining the boundaries of creativity, efficiency, and practicality. On the other hand, it has been suggested that the field of complex molecular assembly is transitioning (or ought to transition) from an

A facile and practical method for the synthesis of trans-(±)-taxifolin and its derivatives via Darzens reaction

• Bo Peng,
• Panpan Yang,
• Maaz Khan,
• Xiaotong Lin,
• Jiang Wu,
• Peng Fu and
• Qingqing Wu

Beilstein J. Org. Chem. 2026, 22, 443–450, doi:10.3762/bjoc.22.31

• in the synthetic route. Therefore, the reaction conditions of 2 and a selected benzaldehyde 3a with two MOM-protected OH groups were optimized. Firstly, various organic and inorganic bases were screened (Table 1). The commonly used organic bases, such as Et3N, DBU, and pyridine, seemed not effective

• compounds. Although HCl is the commonly used acid for this step [19][20][21][22][23][24][25][26][27][28][29][30], we also screened some other acids and the results are collected in Table 2. As can be seen from the table, inorganic acids (Table 2, entries 1 and 2) generally gave better results than organic

Synthesis and anti-cancer activity of naphthalimide–organylselanyl conjugates

• Rajkumar Ravi and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2026, 22, 416–435, doi:10.3762/bjoc.22.29

• washed twice with water (20 mL) and brine (20 mL). The organic layer was dried over anhydrous MgSO₄, and the solution was concentrated under reduced pressure. Slow evaporation of the solvent followed by the addition of methanol afforded the desired compound 10 as a white solid with a yield of 1.2 g, 53

• with water (20 mL) and brine (20 mL). The organic layer was dried with anhydrous MgSO4, filtered and the solvent was evaporated under vacuum. Petroleum ether was added to the residue and triturated. The solid was filtered, affording white amine 11 (500 mg, 48%). mp: 95–97 °C; 1H NMR (400 MHz, CDCl3) δ

• 1.5 h. Thin-layer chromatography (TLC) was used to track the reaction progress. Upon completion of the reaction, ice-cold water was used to quench the reaction mixture, and the mixture was extracted with ethyl acetate. After two water and brine washes, the organic layer was dried over anhydrous

Dialkylaminoalkylation of β-ketosulfones via ring-opening of 3-sulfonylpyrrolidines

• Evgeny M. Buev,
• Alexander V. Pavlushin,
• Vladimir S. Moshkin and
• Vyacheslav Y. Sosnovskikh

Beilstein J. Org. Chem. 2026, 22, 383–389, doi:10.3762/bjoc.22.26

• obtained products with LiAlH4 leads to a substitution of the attached nucleophilic moiety with hydrogen in good yields. Keywords: aminoalkylation; aminosulfones; ketosulfones; pyrrolidines; Introduction Sulfones and sulfonic acids are valuable structural motifs in organic chemistry, notable for their

Electrosynthetic access to unsymmetrical oxaza[8]helicenes with high chiral stability and strong circularly polarized luminescence (CPL)

• Tin Zar Aye,
• Rubal Sharma,
• Muthu Karuppasamy,
• Daiya Suzuki,
• Haruka Nakajima,
• Yoshitane Imai,
• Mitsuhiro Arisawa,
• Mohamed S. H. Salem and
• Shinobu Takizawa

Beilstein J. Org. Chem. 2026, 22, 372–382, doi:10.3762/bjoc.22.25

• Yamada-oka, Suita, Osaka 565-0871, Japan Graduate School of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 8366004, Egypt 10.3762/bjoc.22.25 Abstract

• rings, yielding stable enantiomeric conformers with pronounced optical activity. The combination of rigid helical topology and tunable electronic structure has propelled helicenes into diverse applications, spanning chiral photonics [6][7][8][9], organic electronics [10][11], molecular machines [12

• ]helicenes. Inspired by the superior selectivity and sustainability of organic electrosynthesis as an eco-friendly alternative to conventional oxidative methods [43][44][45][46][47], we leveraged our electrochemical approaches [48][49][50][51][52], and redesigned the synthons to access a new unsymmetrical

Non-central chirality in organic chemistry

• Ken Tanaka and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2026, 22, 370–371, doi:10.3762/bjoc.22.24

• ; chiroptical properties; molecular chirality; Chirality is a foundational concept in organic chemistry, traditionally framed around tetrahedral carbon stereocenters. Over the past decades, however, it has become increasingly clear that molecular handedness is not confined to localized points in space. Axes

• complementary roles played by non-central chiral molecules in contemporary organic chemistry. First, they continue to serve as demanding benchmarks for asymmetric synthesis, probing how far stereochemical information can be transmitted and controlled when the stereogenic element is spatially or conceptually

• the shared concept of chirality beyond central chirality. The open and inclusive scope of the Beilstein Journal of Organic Chemistry provide a particularly suitable platform for such a concept-driven collection, allowing broad connections across subfields of organic chemistry to be explored without

Recent advances in the cleavage of non-activated amides

• Eun-Sol Choi and
• Hyo-Jun Lee

Beilstein J. Org. Chem. 2026, 22, 352–369, doi:10.3762/bjoc.22.23

• Eun-Sol Choi Hyo-Jun Lee Department of Chemistry, Kunsan National University, Gunsan 54150, Republic of Korea 10.3762/bjoc.22.23 Abstract The amide bond is one of the most fundamental and widely utilized functional groups in organic chemistry, central to the structures of pharmaceuticals

• . Keywords: amide; amide activation; esterification; non-activated amide; transamidation; Introduction Serving as a cornerstone in organic chemistry, the amide bond is a fundamental and extensively utilized functional group, playing a central role in natural products, biomolecules, and functional materials

• substitution, making its selective transformation a long-standing challenge in organic synthesis. While strategies for activating twisted amides, bearing electron-withdrawing and sterically demanding substituents on nitrogen, are now well established, general and efficient methods for modifying conventional

Synthesis of tricyclic fused pyrrolidine nitroxides from 2-alkynylpyrrolidine-1-oxyls

• Mark M. Gulman,
• Yuliya F. Polienko,
• Sofia Yu. Trakhininа,
• Yuri V. Gatilov,
• Tatyana V. Rybalova,
• Sergey A. Dobrynin and
• Igor A. Kirilyuk

Beilstein J. Org. Chem. 2026, 22, 344–351, doi:10.3762/bjoc.22.22

• Mark M. Gulman Yuliya F. Polienko Sofia Yu. Trakhininа Yuri V. Gatilov Tatyana V. Rybalova Sergey A. Dobrynin Igor A. Kirilyuk N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk, 630090, Russia Novosibirsk State University, Pirogova Str. 2

• , Novosibirsk, 630090, Russia 10.3762/bjoc.22.22 Abstract Rotational correlation time is a key parameter for organic radical contrast agents (ORCA) for magnetic resonance imaging (MRI). Design of polycyclic systems with incorporated nitroxide moieties in which rotation of the radical separately from the

• components of many high-tech materials, such as energy storage and organoelectronics devices [1][2][3][4][5][6][7][8], catalysts [9][10], bioactive coatings and nanoparticles [11][12], organic radical contrast agents (ORCAs) for magnetic resonance imaging (MRI) [13][14], etc. For these applications, numerous

Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis

• Nicolas Kratena,
• Nicolas Heinzig and
• Peter Gärtner

Beilstein J. Org. Chem. 2026, 22, 289–343, doi:10.3762/bjoc.22.21

• editing; terpenoids; total synthesis; Introduction The vast richness of structural diversity in terpenoid natural products has fascinated organic chemists for more than a century now [1][2][3][4][5]. With more sophisticated techniques for isolation and characterisation emerging over the decades

• secured. Organic synthetic chemistry can help to fill gaps or evaluate, support or revise initially implausible proposed biogenesis routes by attempting to mimic these transformations (= bioinspired or biomimetic synthesis) [11][12][13][14][15][16][17][18]. In general, the biogenesis of unique carbon

Spirobarbiturates with a pyrrolizidine moiety: synthesis, structure and biological evaluation

• Arthur A. Puzyrkov,
• Andrew S. Drachuk,
• Ekaterina A. Popova,
• Alexander V. Stepakov and
• Vitali M. Boitsov

Beilstein J. Org. Chem. 2026, 22, 274–288, doi:10.3762/bjoc.22.20

• ]. Advances in this area of organic synthesis include the preparation of barbiturates containing spiro-fused cyclohexane, cyclopentane, tetrahydrooxepine, and tetrahydroquinoline moieties via [3 + 2], [4 + 2], and [5 + 2] annulation reactions involving arylidene and alkylidene barbiturates [20][21][22][23

• barbiturate moieties of paired enantiomers (see Supporting Information File 1, Tables S2 and S3). The Hirshfeld surface (HS) analysis provides a robust tool for visualizing and characterizing intermolecular interactions in organic crystal lattices. The calculations of the HS were performed using

Arene activation via π-bond localization: concepts and opportunities

• Paul Meiners,
• Julian J. Melder and
• Tobias Morack

Beilstein J. Org. Chem. 2026, 22, 257–273, doi:10.3762/bjoc.22.19

• palladium to aryl halides serving as a prominent example [41]. In addition to such fleeting intermediates, recent decades have seen the emergence of numerous well-defined metal–arene complexes, sufficiently stable to enable systematic exploration of their rich and versatile organic chemistry. η2

• exposure to reaction conditions that more labile systems could not tolerate. Crucially, most reagents used in organic synthesis react preferentially with the arene ligand rather than the metal center [45]. Building on the electronic blueprint established by the osmium system, Harman introduced a new

•  6B) [45]. Application in organic synthesis Organic transformations of η2-coordinated arenes can be broadly divided into three categories, depending on what dictates reactivity: the polarization of the free molecule, the site of metal coordination, or the backbonding interaction itself. Early studies

A mild and atom-efficient four-component cascade strategy for the construction of biologically relevant 4-hydroxyquinolin-2(1H)-one derivatives

• Dmitrii A. Grishin,
• Kseniia I. Sharkovskaia,
• Ilya G. Kolmakov,
• Daria A. Ipatova,
• Rostislav A. Petrov,
• Nikolai D. Dagaev,
• Dmitry A. Skvortsov,
• Maria G. Khrenova,
• Valeriy V. Andreychev,
• Sergei A. Evteev,
• Yan A. Ivanenkov,
• Roman L. Antipin,
• Olga А. Dontsova and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2026, 22, 244–256, doi:10.3762/bjoc.22.18

• ; Introduction Contemporary organic chemistry focuses on the development of universal, efficient, and environmentally benign synthetic methods that address the challenges of constructing complex molecular architectures [1][2][3]. Among these, multicomponent reactions (MCRs) have emerged as powerful tools

Configuration–packing synergy enabling integrated crystalline-state RTP and amorphous-state TADF

• Ruiyan Wang and
• Yunan Wu

Beilstein J. Org. Chem. 2026, 22, 224–236, doi:10.3762/bjoc.22.16

• phosphorescence; thermally activated delayed fluorescence; Introduction Organic light-emitting materials have attracted significant attention due to their remarkable potential across a wide array of applications [1][2][3], such as in display technologies [4], information security and data storage [5], time

• -resolved biological imaging [6], chemical and biological sensing [7], as well as energy transfer and upconversion processes [8]. The unique characteristics of organic materials, including their solubility, ease of processing, molecular structure programmability, and the tunability of their emission color

• excited states, with a particular focus on the generation, migration, and efficient utilization of triplet excitons, which are crucial to device performance. In pure organic systems, the effective utilization of triplet excitons typically proceeds along two primary pathways: room-temperature

Synthesis of diaryl phosphates using phytic acid as a phosphorus source

• Kazuya Asao,
• Seika Matsumoto,
• Haruka Mori,
• Riku Yoshimura,
• Takeshi Sasaki,
• Naoya Hirata,
• Yasuyuki Hayakawa and
• Shin-ichi Kawaguchi

Beilstein J. Org. Chem. 2026, 22, 213–223, doi:10.3762/bjoc.22.15

• soil. It can potentially serve as a phosphorus source in the syntheses of organic phosphates; however, this approach has not been utilized for the preparation of phosphate esters. In this study, we report the first successful synthesis of phosphate esters using phytic acid as a phosphorus source. Crude

• gives a lower yield because the phytic acid forms a syrup-like precipitate in the reaction mixture due to its poor solubility in organic solvents, thereby preventing efficient release of phosphoric acid into the reaction mixture. The plot depicted in Figure 4 shows that there is almost no induction

Screwing the helical chirality through terminal peri-functionalization

• Devesh Chandra,
• Sachin and
• Upendra Sharma

Beilstein J. Org. Chem. 2026, 22, 205–212, doi:10.3762/bjoc.22.14

• of chirality. Molecules with helical chirality impart a crucial role in several biological phenomena as well as in modern materials applications. Classically, the generation of chiral helicity in organic molecules relies on a ring extension by means of cycloaddition and related reactions. Recently

• in their core structure [8]. Point chirality is the simplest form of chirality, and it is relatively easy to control and characterize during the synthesis of organic molecules. Due to these facts point chirality holds a central position among the different types of chirality. Axial chirality is

• another important type of chirality, where the chirality is controlled by restricted rotation among an axis. These types of molecules play an important role as chiral ligands in organic synthesis, i.e., BINOL, BINAP, etc. [9][10][11]. Another form of chirality, where chirality depends on a constrained

Base-promoted deacylation of 2-acetyl-2,5-dihydrothiophenes and their oxygen-mediated hydroxylation

• Vladimir G. Ilkin,
• Margarita Likhacheva,
• Igor V. Trushkov,
• Tetyana V. Beryozkina,
• Vera S. Berseneva,
• Vladimir T. Abaev,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2026, 22, 192–204, doi:10.3762/bjoc.22.13

• Vladimir G. Ilkin Margarita Likhacheva Igor V. Trushkov Tetyana V. Beryozkina Vera S. Berseneva Vladimir T. Abaev Wim Dehaen Vasiliy A. Bakulev TOS Department, Ural Federal University, 19 Mira str., Yekaterinburg 620002, Russia N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of

• Oxidative transformations are an important area of modern organic synthesis [1], producing a broad range of valuable synthetic products for the industry. A variety of catalytic reactions were developed for the oxidative conversions of unsaturated compounds [2][3][4][5], alcohols [6][7], alkanes [8][9][10

• migration in the formed tetrahedral intermediate to afford formate ester; c) hydrolysis of the latter to form phenols [28]. The development of methods for the construction of heterocycles and their modification is an important area of organic synthesis [29]. Although the Dakin oxidation has become a

Improved synthesis and physicochemical characterization of the selective serotonin 2A receptor agonist 25CN-NBOH

• Adrian G. Rossebø,
• Hannah G. Kolberg,
• Anders E. Tønder,
• Louise Kjaerulff,
• Poul Erik Hansen,
• Karla A. Frydenvang,
• Jesper Østergaard and
• Jesper L. Kristensen

Beilstein J. Org. Chem. 2026, 22, 175–184, doi:10.3762/bjoc.22.11

• recrystallized from ethanol (Figure 3, purple), a similar pattern is observed, indicating a high degree of crystallinity. Furthermore, samples of 1·HCl prepared either by rapid precipitation in organic solvents, as described in the Experimental section (red), or material isolated from a saturated solution of 1

• aqueous Na2CO3. The layers were separated, the organic phase collected, and the aqueous phase was further extracted with dichloromethane (3 × 25 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, evaporated in vacuo, and deposited on Celite. Purification by automated flash column

• start of the experiment. Solutions of 2, 0.5, and 0.1 mg/mL of the drug in the buffer solutions at pH 5.00, 7.40, and 9.50, respectively, were prepared. The organic phase was hereafter added to the buffer solution in a ratio of 1:9 at pH 5.00 and 7.40 and 1:19 at pH 9.50. The samples were rotated for 24