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

• File 1. The isolated compounds were characterized via NMR (1H, 13C, 19F, and 31P) and low-resolution mass spectrometry measurements. The NMR measurements were conducted using a Varian NMR 400 MHz system (400 MHz) and a Bruker AVANCE NEO console (400 MHz). Mass spectrometry was performed using LCMS-2020

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

• through a catalytic kinetic resolution (KR) process was developed by Liu and co-workers [32]. The authors screened a range of organocatalysts, i.e., Takemoto’s thiourea catalyst, (S,S)-1,2-cyclohexanediamine-derived thioureas, cinchona alkaloid-derived thiourea, and squaramides to achieve the desired

• enantioselectivity. Notably, [6]helicene 3k was also readily produced, via kinetic resolution (Scheme 1). Computational studies suggested that hydrogen bonding and π interactions between the reactants and catalyst L1 controlled the stereochemical output of the products 3. The catalyst proximate both reactants to

• helical chiral entities was reported by Wang and co-workers. They reported an organocatalyzed asymmetric synthesis of phosphorus-containing chiral helicenes enabled by dynamic kinetic resolution using copper and peptide-mimetic phosphonium salts, i.e. amino acid-derived phosphonium iodide and bromide as

A new synthesis of Tyrian purple (6,6’-dibromoindigo) and its corresponding sulfonate salts

• Holly Helmers,
• Mark Horton,
• Julie Concepcion,
• Jeffrey Bjorklund and
• Nicholas C. Boaz

Beilstein J. Org. Chem. 2026, 22, 167–174, doi:10.3762/bjoc.22.10

• authors wish to thank the University of Notre Dame and Dr. William Bogges for his assistance in obtaining high-resolution mass spectra of synthesized compounds. Moreover, the authors want to thank the 2024 and 2025 Organic Chemistry II classes at North Central College, whose preliminary work served as

Circumventing Mukaiyama oxidation: selective S–O bond formation via sulfenamide–alcohol coupling

• Guoling Huang,
• Huarui Zhu,
• Shuting Zhou,
• Wanlin Zheng,
• Fangpeng Liang,
• Zhibo Zhao,
• Yifei Chen and
• Xunbo Lu

Beilstein J. Org. Chem. 2026, 22, 158–166, doi:10.3762/bjoc.22.9

• previously disclosed a PIDA-mediated oxidative strategy for alcohol incorporation via activation of the S–NH bond (Scheme 1a) [14]. More recently, Wu and co-workers advanced the field by developing a dynamic kinetic resolution protocol for the enantioselective synthesis of sulfinimidate esters from racemic

• exceeds the theoretical maximum of 23% expected from the starting diastereomeric ratio, suggesting that the two diastereomers of 5 did not react at identical rates. These results are consistent with a partial kinetic resolution, wherein the major diastereomer of 5 reacts preferentially, leading to the

• reactivities of the two diastereomers. Although these findings strongly support the occurrence of a partial kinetic resolution, further kinetic measurements would be required for definitive confirmation. A plausible mechanism is outlined as follows. First, the sulfenamide 1 is oxidatively brominated by N

Design and synthesis of an axially chiral platinum(II) complex and its CPL properties in PMMA matrix

• Daiki Tauchi,
• Sota Ogura,
• Misa Sakura,
• Kazunori Tsubaki and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2026, 22, 143–150, doi:10.3762/bjoc.22.7

• spectroscopy, as well as high-resolution mass spectrometry (HRMS). Due to its low solubility, single crystals suitable for X-ray crystallographic analysis could not be obtained. Spectroscopic analysis and DFT calculations To elucidate the electronic structure of the platinum(II) complex, UV–vis absorption

Highly electrophilic, gem- and spiro-activated trichloromethylnitrocyclopropanes: synthesis and structure

• Ilia A. Pilipenko,
• Mikhail V. Grigoriev,
• Olga Yu. Ozerova,
• Igor A. Litvinov,
• Darya V. Spiridonova,
• Aleksander V. Vasilyev and
• Sergey V. Makarenko

Beilstein J. Org. Chem. 2026, 22, 123–130, doi:10.3762/bjoc.22.5

• (1H), 100.53 MHz (13C) in CDCl3 using residual signals of the nondeuterated solvent (δH 7.26, δC 77.16) as the references. The vibrational spectra were measured on a Shimadzu IR-Prestige-21 Fourier-transform IR spectrometer in KBr pellets over 400–4000 cm−1 range (resolution was 2 cm−1). Mass spectra

Total synthesis of natural products based on hydrogenation of aromatic rings

• Haoxiang Wu and
• Xiangbing Qi

Beilstein J. Org. Chem. 2026, 22, 88–122, doi:10.3762/bjoc.22.4

• hydrogenation reaction (Scheme 7) [60]. Using an acid-assisted dynamic kinetic resolution method, they obtained a series of chiral indolines 56 containing exocyclic stereocenters in high yields and excellent enantioselectivity. Mechanistic studies of the reaction revealed that the dynamic kinetic resolution

• the reaction include high functional group tolerance and excellent stereocontrol. In the same year, Zhou and co-workers reported a rhodium/bisphosphine-catalyzed asymmetric hydrogenation reaction of all-carbon aromatic rings 69 (Scheme 8) [64]. Through desymmetrization or kinetic resolution, a series

• the cyano group to an amide (162) under acidic conditions, which then allowed successful Pd/C-mediated hydrogenation to 163. Subsequent dehydration with POCl3 and chiral resolution using ᴅ-DBTA provided the optically enriched compound 165 (Scheme 22). While this approach rendered catalytic

Reactivity umpolung of the cycloheptatriene core in hexa(methoxycarbonyl)cycloheptatriene

• Dmitry N. Platonov,
• Alexander Yu. Belyy,
• Rinat F. Salikov,
• Kirill S. Erokhin and
• Yury V. Tomilov

Beilstein J. Org. Chem. 2026, 22, 64–70, doi:10.3762/bjoc.22.2

• negative free energy changes for all the stages of this reaction. A chlorination experiment with 2,2,6,6-tetramethylpiperidinyloxyl revealed a trace amount of a trap product detected by high-resolution mass spectrometry to support the radical mechanism. However, this does not exclude the possibility of a

Sustainable electrochemical synthesis of aliphatic nitro-NNO-azoxy compounds employing ammonium dinitramide and their in vitro evaluation as potential nitric oxide donors and fungicides

• Alexander S. Budnikov,
• Nikita E. Leonov,
• Michael S. Klenov,
• Andrey A. Kulikov,
• Igor B. Krylov,
• Timofey A. Kudryashev,
• Aleksandr M. Churakov,
• Alexander O. Terent’ev and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2025, 21, 2739–2754, doi:10.3762/bjoc.21.211

• delta (δ) units, parts per million (ppm) downfield from internal TMS (1H, 13C) or external CH3NO2 (14N negative values of δN correspond to upfield shifts). The IR spectra were recorded with a Bruker ALPHA-T spectrometer in the range of 400–4000 cm−1 (resolution 2 cm−1) as pellets with KBr or as a thin

• layer. High-resolution ESI mass spectra (HRMS) were recorded with a Bruker micrOTOF II instrument. Silica gel 60 Merck (15–40 μm) was used for preparative column and thin-layer chromatography. Silica gel “Silpearl UV 254” was used for preparative column and thin-layer chromatography. Analytical thin

Synthesis of new tetra- and pentacyclic, methylenedioxy- and ethylenedioxy-substituted derivatives of the dibenzo[c,f][1,2]thiazepine ring system

• Gábor Berecz,
• András Dancsó,
• Mária Tóthné Lauritz,
• Loránd Kiss,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2025, 21, 2645–2656, doi:10.3762/bjoc.21.205

• . High-resolution mass spectra (HRMS) were recorded on a Bruker Q-TOF MAXIS Impact mass spectrometer coupled with a Waters I-Class UPLC system with a diode array detector. HRMS (TOF MS EI) measurements were performed on an Agilent 2750 GC/Q-TOF mass spectrometer with MSD direct inlet probe. Single

Efficient solid-phase synthesis and structural characterization of segetalins A–H, J and K

• Liangyu Liu,
• Wanqiu Lu,
• Quanping Guo and
• Zhaoqing Xu

Beilstein J. Org. Chem. 2025, 21, 2612–2617, doi:10.3762/bjoc.21.202

• RP-HPLC. This optimized protocol afforded segetalins A–H, J and K (1–10) with 45% to 70% isolated yields (Figure 1). Structural characterization The synthetic compounds 1–10 were rigorously characterized to confirm their identity and purity (see Supporting Information File 1). High-resolution

Rotaxanes with integrated photoswitches: design principles, functional behavior, and emerging applications

• Jullyane Emi Matsushima,
• Khushbu,
• Zuliah Abdulsalam,
• Udyogi Navodya Kulathilaka Conthagamage and
• Víctor García-López

Beilstein J. Org. Chem. 2025, 21, 2345–2366, doi:10.3762/bjoc.21.179

• for precise control over their structural, dynamic, and functional properties. By harnessing light as a non-invasive stimulus with high spatial and temporal resolution, these photoswitches allow for the modulation of the rotaxanes’ intra- and intermolecular interactions, optoelectronic properties, and

Recent advances in Norrish–Yang cyclization and dicarbonyl photoredox reactions for natural product synthesis

• Peng-Xi Luo,
• Jin-Xuan Yang,
• Shao-Min Fu and
• Bo Liu

Beilstein J. Org. Chem. 2025, 21, 2315–2333, doi:10.3762/bjoc.21.177

• -diketones, the rigid lattice structure locks molecules into a specific conformation, limiting access to certain γ-hydrogens for abstraction and thus enhancing regioselectivity [42]. Enantiopure 87 was obtained by preparative chiral supercritical fluid chromatography (SFC) resolution of the racemate, while

A chiral LC–MS strategy for stereochemical assignment of natural products sharing a 3-methylpent-4-en-2-ol moiety in their terminal structures

• Rei Suo,
• Raku Irie,
• Hinako Nakayama,
• Yuta Ishimaru,
• Yuya Akama,
• Masato Oikawa and
• Shiro Itoi

Beilstein J. Org. Chem. 2025, 21, 2243–2249, doi:10.3762/bjoc.21.171

• the MPO moiety by LC–MS and demonstrate its application to the stereochemical assignment of capsulactone (1) at the microgram scale. The strategy involves the optical resolution of MPO derivatives, chemical degradation of 1, and the stereoselective synthesis of four diastereomers. Results and

• complete separation of the stereoisomers was not achieved, the corresponding peaks exhibited improved resolution compared to those of 4 (Figure S2, Supporting Information File 1). To further enhance separation, the p-nitrobenzoyl (PNB) ester 6 was prepared (Scheme 1B). After repeated trials with several

Thiadiazino-indole, thiadiazino-carbazole and benzothiadiazino-carbazole dioxides: synthesis, physicochemical and early ADME characterization of representatives of new tri-, tetra- and pentacyclic ring systems and their intermediates

• Gyöngyvér Pusztai,
• László Poszávácz,
• Anna Vincze,
• András Marton,
• Ahmed Qasim Abdulhussein,
• Judit Halász,
• András Dancsó,
• Gyula Simig,
• György Tibor Balogh and
• Balázs Volk

Beilstein J. Org. Chem. 2025, 21, 2220–2233, doi:10.3762/bjoc.21.169

• using widely accepted strategies [46][47]. DMSO-d6 or CDCl3 were used as the solvents and tetramethylsilane (TMS) as the internal standard. Chemical shifts (δ) and coupling constants (J) are given in ppm and in Hz, respectively. High-resolution mass spectra were recorded on an Agilent 2750 GC/Q-TOF mass

C2 to C6 biobased carbonyl platforms for fine chemistry

• Jingjing Jiang,
• Muhammad Noman Haider Tariq,
• Florence Popowycz,
• Yanlong Gu and
• Yves Queneau

Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165

• 50% yield and 99% ee after kinetic resolution using Escherichia coli (Scheme 57) [189]. Other reactions: Yamamoto synthesized 6-hydroxy-2-(trifluoromethyl)-2H-pyran-3(6H)-ones from furfural via trifluoromethylation using the Ruppert–Prakash reagent (TMSCF3), followed by a photo-Achmatowicz reaction

Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis

• Lihua Wei,
• Rui Yang,
• Zhifeng Shi and
• Zhiqiang Ma

Beilstein J. Org. Chem. 2025, 21, 1932–1963, doi:10.3762/bjoc.21.151

• suppress potential intramolecular acyl migration. To further improve the optical purity of monoester 53, a Pseudomonas aeruginosa lipase-mediated kinetic resolution was performed with ethoxyvinyl butyrate 54, ultimately achieving monoester 53 with 97% ee in 60% yield and the diester 53a. With

• -worker described the asymmetric synthesis of (−)-rasfonin, harnessing an enantioselective enzymatic desymmetrization with lipase AK and an enzymatic oxidative kinetic resolution to install stereocenters [47]. The synthesis commenced with the preparation of fragment 100 from ethylene glycol (97) (Scheme

• functional group manipulations, alcohol 103 was subjected to enzymatic oxidative kinetic resolution with the bacterium Gluconobacter oxydans, producing alcohol 104 and acid 105. The alcohol 104 with the desired C9 stereocenter was then converted into fragment 106 in nine steps, while acid 105 was recycled to

Synthesis of N-doped chiral macrocycles by regioselective palladium-catalyzed arylation

• Shuhai Qiu and
• Junzhi Liu

Beilstein J. Org. Chem. 2025, 21, 1917–1923, doi:10.3762/bjoc.21.149

• yields (ΦF up to 0.69). Furthermore, enantiomeric resolution of inherent chiral MC1 was achieved using preparative chiral HPLC, enabling detailed investigation of its chiroptical behavior through circular dichroism and circularly polarized luminescence spectroscopy. Keywords: dihydroindolocarbazole

• , these macrocycles show blue to green emissions with high fluorescence quantum yields (ΦF up to 0.69). Owing to the existence of inherent chirality, two enantiomers of N-doped macrocycle MC1 were successfully isolated by chiral resolution, enabling detailed investigation of its chiroptical properties

• values up to 0.69. Remarkably, MC1 and MC3 are inherent chiral owing to their C1 symmetric structures. The enantiomers of MC1 were successfully isolated by chiral resolution, which indicate a gabs value of 1.1 × 10−3 and a glum value at the level of 10−4. Our work represents one of the rare examples of

Preparation of spirocyclic oxindoles by cyclisation of an oxime to a nitrone and dipolar cycloaddition

• Beth L. Ritchie,
• Alexandra Longcake and
• Iain Coldham

Beilstein J. Org. Chem. 2025, 21, 1890–1896, doi:10.3762/bjoc.21.146

• ) are quoted to the nearest 0.5 Hz with values in hertz (Hz). 13C NMR spectra were recorded on the above instrument at 100 MHz. Low- and high-resolution (accurate mass) mass spectra were recorded on a Walters LCT instrument using electrospray ionisation (ESI). Synthesis of the aldehyde 4 Sc(OTf)3 (0.63

Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules

• Wei Liu and
• Xiaoyu Yang

Beilstein J. Org. Chem. 2025, 21, 1864–1889, doi:10.3762/bjoc.21.145

• without the CPA catalyst. Notably, indolohelicenoid 23e could effectively be converted into the fully aromatic indolohelicene 24e under DDQ-mediated oxidative conditions without compromising the enantiopurity of the compound. Kinetic resolution stands as one of the most practical and efficient strategies

• ]. While CPAs have been extensively utilized in kinetic resolution of centrally chiral [26][27][28] and axially chiral compounds [29], their application in the kinetic resolution of helically chiral compounds remains largely unexplored. In 2024, Liu and co-workers developed an effective method for

• catalytic kinetic resolution of racemic helical polycyclic phenols through an organocatalyzed enantioselective dearomative amination reaction [30]. The racemic polycyclic phenol derivatives 25, which exist as single diastereomers featuring both central chirality and helical chirality, were readily prepared

Systematic pore lipophilization to enhance the efficiency of an amine-based MOF catalyst in the solvent-free Knoevenagel reaction

• Pricilla Matseketsa,
• Margret Kumbirayi Ruwimbo Pagare and
• Tendai Gadzikwa

Beilstein J. Org. Chem. 2025, 21, 1854–1863, doi:10.3762/bjoc.21.144

• Kansas State University for the acquisition of the NMR spectrometer (Grant CHE-1826982) used in this study. We thank the Ping Li Lab for high-resolution mass spectrometry, and the NIH for the grant (R01GM117259-01S1) which partially funded the purchase of the instrument.

Research progress on calixarene/pillararene-based controlled drug release systems

• Liu-Huan Yi,
• Jian Qin,
• Si-Ran Lu,
• Liu-Pan Yang,
• Li-Li Wang and
• Huan Yao

Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139

• Light-responsive controlled release Light is an ideal external stimulus due to its ease of use, low cost, and safety [110][111]. Its unique advantages include being easily turned on and off, providing high spatial and temporal resolution with precise control over irradiation wavelength and intensity

Convenient alternative synthesis of the Malassezia-derived virulence factor malassezione and related compounds

• Karu Ramesh and
• Stephen L. Bearne

Beilstein J. Org. Chem. 2025, 21, 1730–1736, doi:10.3762/bjoc.21.135

• reporting NMR spectral data are: bm, broad multiplet; bs, broad singlet; bt, broad triplet; d, doublet; dd, doublet of doublets; m, multiplet; q, quartet; s, singlet; and t, triplet. High-resolution (HR) electrospray ionization (ESI) mass spectra (MS) were collected using a Bruker microTOF Focus orthogonal

Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides

• Tsun-Yi Chiang,
• Mei-Huei Lin,
• Chun-Wei Chang,
• Jinq-Chyi Lee and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2025, 21, 1671–1677, doi:10.3762/bjoc.21.131

• pattern aligns with existing literature and is corroborated by our X-ray analysis. High-resolution electrospray ionization mass spectrometry confirmed the molecular mass, showing spectral peaks aligning with the calculated mass ([M + Na]+ calcd for C72H78N4O23Na, 1389.4949; found, 1389.4943). Conclusion

Catalytic asymmetric reactions of isocyanides for constructing non-central chirality

• Jia-Yu Liao

Beilstein J. Org. Chem. 2025, 21, 1648–1660, doi:10.3762/bjoc.21.129

• unsymmetrical diisocyanide was used, the initial isocyanide insertion was found to be non-regioselective, delivering a 1:1 mixture of regioisomers (17c and 17c’). Intriguingly, 17a could act as a chiral acylating reagent, applying in the kinetic resolution of racemic primary amines rac-18. Additionally, after

• reaction between alkene 43 and 2,2′-dienone 44. The corresponding spirooxindole 45 was obtained in >19:1 dr, 63% yield, and 89% ee. Dynamic kinetic resolution of configurationally labile bridged biaryls The catalytic asymmetric dynamic kinetic resolution (DKR) of configurationally labile bridged biaryls

• Groebke–Blackburn–Bienaymé reaction. Construction of axially chiral 3-arylpyrroles via de novo pyrrole formation. Synthesis of atropoisomeric 3-arylpyrroles via central-to-axial chirality transfer. Dynamic kinetic resolution of bridged biaryls with α-acidic isocyanides. Desymmetrization of prochiral