Search results
Search for "selective" in Full Text gives 1551 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Gold extraction at the molecular level using α- and β-cyclodextrins
Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89
- . Practical applications of this ability are directed to the selective isolation of gold from a variety of sources, spanning from gold-rich mining ores and tailings/mining wastes to gold-bearing metal scraps obtained from disposed electronic devices. Moreover, it describes the development of a method based on
- sections of this review. The combination of interactions linking cyclodextrin channels with infinite polymer chains of tetrahaloaurate ions and their counterions affords a highly specific and stable superstructure that is the working pillar for the efficient and selective process of gold recovery from
- by hydrogen-bond interactions and oriented in alternating head-to-head and tail-to-tail modes comprising a continuous channel filled by an alternating [K(OH2)6]+ and [AuBr4]− polyionic chain (Figure 1). The authors further demonstrated that the process is selective for gold by determining, using ICP
Recent advances in synthetic approaches for bioactive cinnamic acid derivatives
Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85
- the past five years is presented, particularly emphasizing the active scaffolds of bioactive cinnamic acid derivatives. The review provides a strategic overview of alternative synthetic routes and highlights the latest innovations, including more efficient, highly selective, and environmentally
- acid possesses three distinct functional groups: carboxyl, alkenyl, and aromatic (Scheme 1). Therefore, highly selective reaction strategies are immensely desired for cinnamic acid derivatizations, preventing other functional groups from interfering. This review is partitioned into specific
- significantly to the efficient and cost-effective production of cinnamic acid derivatives. This review focuses on diverse, one-step strategies to access cinnamic acid derivatives with more efficient, highly selective, and sustainable approaches. By examining recent advancements in the design and synthesis of
Recent total synthesis of natural products leveraging a strategy of enamide cyclization
Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81
- the terminal alkene and the conformational strain of forming a bridge[3.2.1]bicycle might be responsible for a selective 6-exo-trig cyclization. From tricyclic compound 4, anti-Markovnikov oxidation catalyzed by palladium led to the formation of aldehyde 5. When treated with p-TsOH, the intramolecular
- divergent total synthesis of several Cephalotaxus alkaloids. The α-hydroxylation of cyclopentanone, followed by amide reduction and methanol elimination in one-pot, produced (−)-cephalotaxine in 9 steps. Alternatively, Riley SeO2 oxidation of 31, benzylic bromination/hydrolyzation, facial selective ketone
On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals
Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80
Studies on the syntheses of β-carboline alkaloids brevicarine and brevicolline
Beilstein J. Org. Chem. 2025, 21, 955–963, doi:10.3762/bjoc.21.79
- ester 29 gave pyrrolo-β-carboline 30 in excellent yield (Scheme 7). Our attempts for the selective saturation of the pyrrole ring of 30 by catalytic reduction were unsuccessful. When the hydrogenation was carried out under mild conditions (ambient temperature, 15 bar H2) in the presence of PtO2.H2O
- ) were also ineffective. Based on literature data [42][43], we attempted the selective reduction of the pyrrole ring of compound 30 with NaCNBH3 in TFA as well. Surprisingly, trifluoroethylated product 32 was isolated. The formation of this compound can also be explained on the basis of analogies
Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes
Beilstein J. Org. Chem. 2025, 21, 947–954, doi:10.3762/bjoc.21.78
- ring was opened in a diastereoselective (SN2 type) and exo-selective manner by a trifluoroacetate anion. The trifluoroacetate anion was conveniently derived from (bis(trifluoroacetoxy)iodo)benzene (PIFA), which was used as the stoichiometric oxidant in the reaction. Overall, this amounted to a highly
- single regioisomer and diastereomer of B was formed (within the limits of 1H NMR detection), attesting to very selective reactivity. Here and in related projects, we found that many I(III) sources could generate a nitrenium ion, including iodosobenzene (PhIO) and iodomesitylene diacetate. However, unless
- , which attacks the pendant olefin to form an aziridinium cation (Scheme 2). A sulfonate counter-anion then opens this aziridinium ring in an exo-selective, SN2 reaction. We were successful in scaling the reaction from 0.3 mmol to 11.5 mmol (38-fold increase) without any erosion in yield or selectivity
A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids
Beilstein J. Org. Chem. 2025, 21, 926–934, doi:10.3762/bjoc.21.75
- reactivity of those two alcohols toward oxidation allowed for the selective conversion of desired alcohol to ketone 24 using PCC, producing a 50% overall yield, while the recovered undesired alcohol could be reverted to 21 by Swern oxidation. Direct enol triflation (Et3N/Tf2O, NaH/PhNTf2, DTBMP/Tf2O, etc
Recent advances in controllable/divergent synthesis
Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73
- insertion to achieve C3 selectivity, whereas nickel catalysis involved alkene isomerization to generate a (2,3-dihydropyrrolyl) intermediate Int-35, followed by C2-selective coupling. In 2024, the Zheng group reported a catalyst-controlled cyclization reaction of bicyclo[1.1.0]butanes (BCBs) 32 with α
- activation induces selective migration of the less sterically hindered secondary carbon center with concomitant dinitrogen elimination, yielding 3-aza-BCHepe as the final product. Solvent control The solvent microenvironment emerged as a critical determinant in governing stereochemical outcomes, exerting
- achieved selective synthesis of either enantiomer of a target product by controlling the reaction duration (Scheme 13) [42]. When performing the asymmetric intermolecular allylic amination of 6-hydroxyisoquinoline (49) with tert-butyl(1-phenylallyl)carbonate ((rac)-50) using an Ir catalyst derived from [Ir
Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions
Beilstein J. Org. Chem. 2025, 21, 884–889, doi:10.3762/bjoc.21.72
- carbon skeletons of many dicarboxylates make selective recognition particularly difficult. To address these challenges, we envisioned that ultracycles composed of macrocycles with anion-binding capabilities could serve as suitable hosts for efficient and selective dicarboxylate recognition. In this study
- introduction of lower-rim hydroxy substituents effectively enhances the dicarboxylate binding through cooperative hydrogen bonding and anion–π interactions. The selective recognition of long and flexible dicarboxylates holds exciting promise for the use of dicarboxylate sensors in medicine and industry. (a, b
Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes
Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71
- organoboron compound with CuOt-Bu and subsequent SN2’-selective allylic alkylation of 1. The densely functionalized structure of these dimerization products offers a versatile synthetic handle for further chemoselective functionalization. Considering the presence of two enolizable esters together with the
- details). In contrast, the use of CsF in dioxane at 70 °C proved to be efficient and selectively provided cyclopropane 9 in good yield, albeit with no diastereoselectivity (Table 2, entry 1). Cs2CO3 was also selective for this cyclization and provided a slight increase in diastereoselectivity, although
- . However, when the reaction was carried out with KOt-Bu, we observed the selective conversion of 9 into product 20 featuring a different cyclopropane scaffold. Slight modification of the reaction conditions allowed us to obtain product 20 in 56% yield as a single diastereomer (Scheme 5a). Taking advantage
Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters
Beilstein J. Org. Chem. 2025, 21, 854–863, doi:10.3762/bjoc.21.69
- prohibitively high in energy for selective reactivity [5]. The inception of energy transfer catalysis (EnT) has expedited discoveries concerning the photoactivation of organic molecules [15][16][17], enabling direct access to the triplet excited state through the use of a photocatalyst (Figure 1A, top
- achieved. It is pertinent to note the enhanced levels of diastereoselectivity obtained for this reaction further underscore the potential of gold catalysts for future EnT reactions. Control reactions indicate selective activation of the α,β-unsaturated ester (see Supporting Information File 1 for full
Unraveling cooperative interactions between complexed ions in dual-host strategy for cesium salt separation
Beilstein J. Org. Chem. 2025, 21, 845–853, doi:10.3762/bjoc.21.68
- dual-host systems for selective ion separation. Keywords: anion binding; cesium extraction; dual-host strategy; ion-pair interaction; solid–liquid extraction; Introduction Ion-pair interaction, defined as the electrostatic attraction between a positively charged cation and a negatively charged anion
- ]. According to our previous results, the binding affinity of L with chloride, sulfate and phosphate is determined to be 2.2 × 102 M−1, 9.9 × 104 M−1, and 3.8 × 106 M−1, respectively (in DMSO) [31]. Such strong anion binding affinity has led to selective extraction of sulfate and phosphate from basic aqueous
- accessibility of the dual-host strategy and suggest that cooperative interactions between receptor-complexed ions can be fine-tuned for selective ion separation. Ongoing work aims to explore diverse combinations of anion and cation receptors for targeted ion separation applications. (a) Schematic illustration
Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers
Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63
- Seeun Lim Teresa Kim Yunmi Lee Department of Chemistry, Kwangwoon University, Seoul 01897, Republic of Korea 10.3762/bjoc.21.63 Abstract This study introduces a highly selective hydrocyanation method based on copper-catalyzed hydroalumination of allenes with diisobutylaluminum hydride, followed
- with diverse functional groups [12][13][14]. Consequently, the development of selective and predictable strategies for the introduction of cyano groups into quaternary carbon frameworks has become necessary in organic synthesis. The transition-metal-catalyzed hydrocyanation of carbon–carbon double
- -system configuration promotes selective functionalization, enabling the synthesis of various complex products through a single transformation [17][18][19]. Therefore, allenes have become versatile intermediates in numerous transition-metal-catalyzed reactions [20][21]. Despite extensive studies on the
Recent advances in the electrochemical synthesis of organophosphorus compounds
Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61
- activities. Budnikova et al. [50] reported a C–P bond formation via the reaction of acridine compounds with trialkyl phosphites in electrochemical conditions without metal catalysts and strong oxidizing reagents, conducting selective C9 phosphorylation with high yield. The reaction was carried out in an
New advances in asymmetric organocatalysis II
Beilstein J. Org. Chem. 2025, 21, 766–769, doi:10.3762/bjoc.21.60
- contributions in stereoselective organocatalytic transformations. The collection contains nine articles featuring various aspects of asymmetric organocatalysis. In the first contribution, Waser et al. examined how chiral phase-transfer catalysts promote β-selective additions of azlactones to allenoates. Maruoka
Copper-catalyzed domino cyclization of anilines and cyclobutanone oxime: a scalable and versatile route to spirotetrahydroquinoline derivatives
Beilstein J. Org. Chem. 2025, 21, 749–754, doi:10.3762/bjoc.21.58
- report the copper-catalyzed synthesis of tetrahydroquinoline derivatives via a domino reaction of aniline with cyclobutanone oxime. This method demonstrates a selective approach for generating bioactive tetrahydroquinoline scaffolds, which have broad applications in pharmaceutical chemistry. The reaction
Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion
Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57
- potency as inhibitors of Man-specific bacterial adhesion investigated. Results and Discussion Synthesis For the preparation of the homobivalent glycocluster 6αMan3αMan 2, the known mannosyl thioacetate 7 [31] was prepared from the trichloroacetimidate 6 [32] and thioacetic acid in an α-selective reaction
- Table 1 shows that the PSS values of the bis-azobenzene glycoclusters 1 and 2 are in a similar range. Furthermore, the glycoazobenzene antennas comprised in 1 and 2 show a similar switching behavior as the individual antennas 6αMan 3, 6βGlc 4, and 3αMan 5. Wavelength-selective photoswitching of 2 as
- to the O-azobenzene (AB) photoswitch. (Orthogonal) photoswitching alters the relative spatial orientation of the two sugar units. Glucose (Glc) moieties are colored in blue and mannose (Man) in green according to the symbol nomenclature for carbohydrates (SNFG) [29][30]. A: Wavelength-selective
Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups
Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55
- weakly. The ratio of the binding constants of a common guest to C1 versus M1 is as follows: Me6PDA (26.0), Me6HDA (22.2), PXDA (4.2), Me6PXDA (3.3), CHDA (2.3), Me6CHDA (1.3), AdA (1.2), Me3AdA (1.1). The C1 host is both a tighter and more selective host for the narrower guests than M1. We can also tease
Origami with small molecules: exploiting the C–F bond as a conformational tool
Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54
- that it is not selective towards injured tissue: it also binds to μ-opioid receptors in healthy tissue, causing side-effects. To overcome this drawback, a fluorinated analogue of fentanyl ((±)-105) was developed [177]. The electron-withdrawing fluorine substituent of 105 lowers the pKaH of the
Recent advances in allylation of chiral secondary alkylcopper species
Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51
- transmetalation of organolithium and organoboron compounds, copper hydride catalysis, and enantiotopic-group-selective transformations of 1,1-diborylalkanes. Detailed mechanistic insights into stereochemical control and current challenges in this field are also discussed. Keywords: allylic substitution; chiral
- generating configurationally unstable organocopper species with secondary carbon–metal bonds, their unique properties, and related mechanistic insights. This review also aims to outline future research directions and prospects, contributing to the development of more efficient and selective copper-catalyzed
- (+)-lasiol was achieved through a highly selective SN2 substitution (SN2/SN2' = >99:1, dr = 98:2, 99% ee), while the preparation of (+)-13-norfaranal and (+)-faranal showcased the versatility of the methodology in constructing more complex terpene frameworks. These successful applications in natural product
Photocatalyzed elaboration of antibody-based bioconjugates
Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49
- conjugation methods often face challenges related to site-selectivity and heterogeneous product mixtures, highlighting the need to develop new, innovative chemical strategies. Photoredox chemistry emerges as a powerful tool in this context, enabling precise, mild, and selective modifications of peptides and
- selective chemical reactions, often for bioconjugation, by utilizing photoaffinity reagents. These reagents are typically photoreactive molecules that can be activated by light to form covalent bonds with nearby molecules [31][32][33]. PAL involves using a light-activated group (often a photo-crosslinker
- ) that can form covalent bonds when exposed to UV or visible light. These photoaffinity tags or crosslinkers are designed to bind to specific biomolecules, such as proteins, nucleic acids, or lipids, in a highly selective manner. The light irradiation triggers a chemical reaction, such as a bond
Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities
Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48
- , epidermoid carcinoma A431, ovarian carcinoma SKOV-3, and breast cancer MCF-7 cell lines. Compounds 2 and 3 exhibited significant cytotoxicity against all the tested cells. Some of the semisynthetic derivatives were also tested for their nematicidal activity and compound 4 displayed significant and selective
- compound 2. This suggests that the presence of the exo-methylene group is a critical structural feature that influences the cytotoxic activity, as outlined earlier [15]. These data also demonstrate possible selective effects of acylated massarilactone D in biological systems. Massarilactone D 3,4,7-tri-O
- -bromobenzoyl (4) also showed significant and selective nematicidal activity with LD90 and LD50 of 100 and 12.5 µg/mL, respectively. In the case of compound 5, the LD90 was not obtained but the LD50 was determined to be 100 µg/mL. Compounds 1, 6, 7, and 8 showed some mortality at concentrations of 50 and 100 μg
Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions
Beilstein J. Org. Chem. 2025, 21, 601–606, doi:10.3762/bjoc.21.47
- scaffold of simonsol C, utilizing an alkaline dearomatization as the key reaction, followed by a functional-group-selective Wittig reaction and concurrent oxy-Michael addition [6]. A bromophenol acetal was used in the intramolecular alkylative dearomatization, which was first reported by Magnus et al. [8
Formaldehyde surrogates in multicomponent reactions
Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45
- byproducts (Scheme 26b) [76][78]. Because of the tendency of formaldehyde to generate these byproducts, several efforts have been made to optimize the chemoselectivity of the Kabachnik–Fields reaction. In this context, Zhao et al. proposed a more selective strategy for the synthesis of α-amino phosphorus
- amine with two methyl groups and a benzyl or allyl group, the cleavage of the N–CH2Ph and N–allyl bond takes place more selective (by 85% and 67%, respectively), instead of the cleavage of an N–Me bond. This explains the high selectivity observed for some examples in Scheme 27. Finally, this methodology
Vinylogous functionalization of 4-alkylidene-5-aminopyrazoles with methyl trifluoropyruvates
Beilstein J. Org. Chem. 2025, 21, 533–540, doi:10.3762/bjoc.21.41
- compounds is a significant and important reaction for the selective synthesis of homoallylic alcohols in an efficient and sustainable way [2][3]. As carbonyl compounds, alkyl trifluoropyruvates [4][5] are an interesting class of compounds that have been used in addition reactions of different nucleophiles
Other Beilstein-Institut Open Science Activities
