Methodology for awakening the potential secondary metabolic capacity in actinomycetes

• Shun Saito and
• Midori A. Arai

Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69

• -acyltransferase polyketide synthase biosynthetic gene cluster sdl (80 kb) from Streptomyces sp. B59 was cloned and transferred into a heterologous host, Streptomyces albus J1074, resulting in the production of a class of polycyclic macrolide shuangdaolides A (1), B, and D and dumulmycin (2) [29]. Furthermore

• ansaseomycins A (3) and B. A number of factors associated with the biosynthetic gene clusters of secondary metabolites regulate their expression; thus, controlling these factors can also be used to activate secondary metabolism (Figure 2b). For example, the production of some secondary metabolites in

• et al. applied a fluorescence-based DNA cleavage assay coupled with HiTES to Streptomyces clavuligerus and identified the steroid 11α-hydroxyprogesterone (14) as an effective elicitor and characterized 10 cryptic enediyne-derived natural products, designated clavulynes A (15) and B–J with unusual

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• and enhance the antiepileptic effect of diazepam. The mechanism of action involved γ-aminobutyric acid (GABA) [38][39][40]. The brain-derived neurotrophic factor (BDNF)–tropomyosin receptor kinase B (TrkB) pathway is closely associated with epilepsy. Crocin can increase the BDNF level in the cortex of

• . The CsCCD2(S323A) mutant could also catalyze the conversion of β-carotene (6) to 1 [91]. BdCCD4.1 and BdCCD4.3, the homologs of CsCCD2 from B. davidii, were discovered by bioinformatic analysis. In vitro and in vivo experiments demonstrated that these two enzymes could cleave zeaxanthin (7), but the

• 2020, Xu et al. conducted a multiomics analysis of 19 ALDH genes from G. jasminoides. Among them, GjALDH2C3 was highly expressed in the fruit and flower of G. jasminoides and showed a coexpression pattern with GjCCD4a [96]. Subsequently, Diretto et al. identified BdALDH from B. davidii and confirmed

Substrate specificity of a ketosynthase domain involved in bacillaene biosynthesis

• Zhiyong Yin and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2024, 20, 734–740, doi:10.3762/bjoc.20.67

• organism shares the same habitat with the predator Myxococcus xanthus that feeds on other bacteria including B. subtilis, and bacillaene is the primary factor conferring B. subtilis cells resistance to predation by M. xanthus [8]. The identification of its biosynthetic gene cluster (bae) revealed that the

• cooperate with the PKS “in trans” [11][12]. Notably, in B. subtilis the giant bacillaene biosynthesis machinery forms an organelle-like complex that can be observed through cryoelectron microscopy [13]. The structure elucidation of “bacillaene” through extensive NMR spectroscopic methods revealed the

• , showing that the amino acid sequences of these KSs correlate with the structures of the processed PKS intermediates up to the β-carbon [20]. 13C NMR spectra of (R)-11 incubated with BaeJ-KS2 and BaeJ-KS2-C222A. A) Free 11 dissolved in incubation buffer; B) (R)-11 bound to BaeJ-KS2 after incubation and

Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

• Senze Qiao,
• Zhongyu Cheng and
• Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

• strategy has been widely employed in the TE domains characterization and chemoenzymatic synthesis of other bioactive macrocyclic peptides, such as surfactin [40], streptogramin B [41], cereulide [42], seongsanamide E [43], etc. In 2005, Marahiel and co-workers accomplished the chemoenzymatic synthesis of

• type B streptogramin variants [41], including pristinamycin IE (8), which belongs to the class of depsipeptide antibiotics. Similarly, the linear peptide-SNAC was prepared through the SPPS method on 2-chlorotrityl resin, and macrolactonization was catalyzed by SnbDE TE, a thioesterase from

• , resulting in daptomycin (12) formation with a ratio of cyclization to hydrolysis of 3:1 (Scheme 4a). The significance of single amino acids for daptomycin bioactivity was evaluated, for instance, the substitution of ʟ-3-MeGlu12 by ʟ-Glu12 in Dap yielded a 7-fold increase of the MIC against B. subtilis

Genome mining of labdane-related diterpenoids: Discovery of the two-enzyme pathway leading to (−)-sandaracopimaradiene in the fungus Arthrinium sacchari

• Fumito Sato,
• Terutaka Sonohara,
• Shunta Fujiki,
• Akihiro Sugawara,
• Yohei Morishita,
• Taro Ozaki and
• Teigo Asai

Beilstein J. Org. Chem. 2024, 20, 714–720, doi:10.3762/bjoc.20.65

• GGPP, followed by hydrolysis by acid phosphatase. GC–MS analysis revealed that AsCPS synthesizes the same product to ObCPS_11g (see Supporting Information File 1, Figure S4A and B). It should be noted that the stereochemistry of CPP needs further verification due to the lack of chiral resolution of our

• bifunctional TCs instead of gene duplication TCs can also be considered (Figure 5B, model b). Conclusion Through genome mining of LRDs in fungi, we identified a unique pair of TCs in which domain organizations are distinct from those of known fungal TCs involved in the related pathways. Heterologous expression

• organizations were discovered, these enzymes would be useful to discuss and further analyze the evolution of TCs in fungi. LRDs in fungi. A) Chemical structures of representative fungal LRDs. B) Reactions catalyzed by selected fungal bifunctional TCs. Sequence analysis of AsPS and AsCPS. A) Biosynthetic gene

SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes

• Julien Borrel and
• Jerome Waser

Beilstein J. Org. Chem. 2024, 20, 701–713, doi:10.3762/bjoc.20.64

• acid B(OTFE)3 had a detrimental effect (Table 7, entry 7). Increasing the stoichiometry of BF3 to 2 equivalents lowered the yield significantly (Table 7, entry 8). In contrast, the loading could be reduced to 30 mol % without impacting the formation of 4a (Table 7, entries 9 and 10). Finally, a fine

New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• aspartate residue as a query, Nett et al. performed genome mining of photoreactive siderophores and isolated two such siderophores, variochelins A and B, from the soil bacterium Variovorax boronicumulans [5]. The Variovorax spp. belonging to plant growth-promoting rhizobacteria (PGPR) enhance plant

• this study, we isolated three new congeners of variochelin-type siderophores, variochelins C–E (3–5), along with two known compounds, variochelins A (1) and B (2), from Variovorax sp. Their structures were elucidated by a combination of NMR, ESIMS/MS, and chemical derivatization. The analysis of the

• -guanidino-3-hydroxy-2-methylheptanoate, indicating that the N-terminal fatty acyl group is a tetradecanoic acid in 2 (Figure 1 and Figure S10 in Supporting Information File 1). Therefore, compound 2 is concluded to be the known lipohexapeptide variochelin B [5]. Compound 3 has the chemical formula of

Evaluation of the enantioselectivity of new chiral ligands based on imidazolidin-4-one derivatives

• Jan Bartáček,
• Karel Chlumský,
• Jan Mrkvička,
• Lucie Paloušová,
• Miloš Sedlák and
• Pavel Drabina

Beilstein J. Org. Chem. 2024, 20, 684–691, doi:10.3762/bjoc.20.62

• , Table 3 summarises the results of Henry reactions obtained by catalysis with copper(II) complexes of ligands IIIa,b. The mutual comparison of these catalysts with those composed of analogous 2-(pyridin-2-yl)imidazolidin-4-ones [5] follows several significant conclusions. For instance, the catalyst of

• IIIa,b led to a lower reaction rate compared to their pyridine counterparts. However, the cis diastereomer (IIIb) showed significantly enhanced enantioselectivity compared to its equivalent pyridine-based ligand with the same configuration (see Supporting Information File 1, part S5). This change from

Regioselective quinazoline C2 modifications through the azide–tetrazole tautomeric equilibrium

• Dāgs Dāvis Līpiņš,
• Andris Jeminejs,
• Una Ušacka,
• Anatoly Mishnev,
• Māris Turks and
• Irina Novosjolova

Beilstein J. Org. Chem. 2024, 20, 675–683, doi:10.3762/bjoc.20.61

• preparation of 2-chloro-4-sulfonylquinazolines 8 (Scheme 3). The starting material 7 underwent SNAr reactions with sodium sulfinates and the C4-substituted products 8a,b were isolated [24]. The complete conversion was achieved in DMF or DMSO. In the case of sodium dodecylsulfinate, the reaction stopped at 70

Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines

• Geng-Xin Liu,
• Xiao-Ting Jie,
• Ge-Jun Niu,
• Li-Sheng Yang,
• Xing-Lin Li,
• Jian Luo and
• Wen-Hao Hu

Beilstein J. Org. Chem. 2024, 20, 661–671, doi:10.3762/bjoc.20.59

• intermediate B should be ruled out from this methodology (Scheme 4b). The product Z-6i was subjected to the standard conditions, but Z-6i was obtained in 100% recovery yield. Therefore, the E/Z selectivity of the MCRs with allenes could be determined by the allylic substitution process (Scheme 4c). Using HPd

• , hydride shift process, and photoinduced homolytic cleavage of the C–Pd bond, furnishing hybrid α-ester alkylpalladium radical I. In path b, upon irradiation with blue light, photoexcited Pd(0)Ln* reduces ethyl diazoacetate (1a) to Pd-radical species I by a proton-coupled electron transfer (PCET) process

• diverse derivatizations further highlight the practical utility of this MCR protocol. Background (a and b) and proposed carboamination MCR with diazo esters (c). a) Selected bioactive γ- and ε-amino acid derivatives. b) Multicomponent reaction strategies with diazo compounds. c) Our design: a radical MCR

Enhanced reactivity of Li⁺@C₆₀ toward thermal [2 + 2] cycloaddition by encapsulated Li⁺ Lewis acid

• Hiroshi Ueno,
• Yu Yamazaki,
• Hiroshi Okada,
• Fuminori Misaizu,
• Ken Kokubo and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2024, 20, 653–660, doi:10.3762/bjoc.20.58

• , 861.08866. HOMO levels of unsaturated substrates and LUMO levels of fullerenes computed at the B3LYP/6-31G(d) level of theory. HPLC profiles of themal [2 + 2]reaction of Li+@C60 with substrate 1 (a) and 2 (b) in o-dichlorobenzene at room temperature. HPLC profiles of 5a (a) and 5b (b) before and after

• photoirradiation at room temperature. 1H-1H 2D-NOESY NMR spectrum (600 MHz, CD2Cl2) of 5a (a) and NOE correlations between two protons. The spectrum (700 MHz, CD2Cl2) of 5b is shown in (b). Cyclic voltammograms of 5a, 5b, and Li+@C60 TFSI− with the potentials relative to the ferrocene/ferrocenium (Fc/Fc

Isolation and structure determination of a new analog of polycavernosides from marine Okeania sp. cyanobacterium

• Kairi Umeda,
• Naoaki Kurisawa,
• Ghulam Jeelani,
• Tomoyoshi Nozaki,
• Kiyotake Suenaga and
• Arihiro Iwasaki

Beilstein J. Org. Chem. 2024, 20, 645–652, doi:10.3762/bjoc.20.57

• novel macrolide glycosides, polycavernosides A (2) and B (3), were reported as the causative compounds for the illness [1]. After that, the second fatal food poisoning incidents occurred in the Philippines caused by the ingestion of polycavernoside A (2)-contaminated red algae [2]. Subsequently

Production of non-natural 5-methylorsellinate-derived meroterpenoids in Aspergillus oryzae

• Jia Tang,
• Yixiang Zhang and
• Yudai Matsuda

Beilstein J. Org. Chem. 2024, 20, 638–644, doi:10.3762/bjoc.20.56

• structural diversity of fungal meroterpenoids and potentially aiding the functional characterization of these tailoring enzymes. Biosynthesis of selected fungal meroterpenoids. (A, B) Dearomatizing prenylation reactions in the biosynthesis of (A) 3,5-dimethylorsellinic acid (DMOA)- and (B) 5-methylorsellinic

• : farnesyl pyrophosphate; FAD: flavin adenine dinucleotide; NADPH: nicotinamide adenine dinucleotide phosphate. (B) HPLC profiles of the metabolites from Aspergillus oryzae transformants. The chromatograms were extracted at 254 nm. (C) Structures of metabolites detected or isolated in this study. Note that

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

• Luan A. Martinho and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

• ], pyrazolo-fused benzophenazines [45], 4,5-dioxopyrrolidines [46], 1,2-dihydropyridine (1,2-DHPs) [47], pyrimido[4,5-b]quinoline-tetraones [48], tetrahydrobenzo[b]pyrans and indazolo[2,1-b]phthalazinetriones [49]. Herein, we report the synthesis of imidazo[1,2-a]pyridines via the GBB-3CR using HPW as

• imidazo[1,2-a]pyridine core [13]. Examples of application of HPW as catalyst in the synthesis of heterocyclic compounds through multicomponent reaction approaches. a) Reported phosphomolybdic acid-catalyzed synthesis of imidazo[1,2-a]pyridines via GBB-3CR. b) Attempts to reproduce the results reported in

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

• Andrew D. Gillie,
• Matthew G. Wakeling,
• Bethan L. Greene,
• Louise Male and
• Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

• Andrew D. Gillie Matthew G. Wakeling Bethan L. Greene Louise Male Paul W. Davies School of Chemistry, University of Birmingham, Birmingham, B15 2TT, UK 10.3762/bjoc.20.54 Abstract A polysubstituted 3-aminoimidazo[5,1-b]oxazol-6-ium framework has been accessed from a new nitrenoid reagent by a two

• particularly underinvestigated [2][18][19]. In this work we report the preparation of a new L-shaped NHC motif, the 3-aminoimidazo[5,1-b]oxazol-5-ylidene A (shortened hereafter to AImOx), which fuses two π-rich rings and positions a sulfonamide group alongside the metal centre (Figure 1b). We envisaged that

• the potential NHC precursor to A, a polysubstituted 3-aminoimidazo[5,1-b]oxazol-6-ium motif B, might be rapidly accessed from an ynamide by sequential oxazole-forming annulation and imidazolium formation steps. The basis of this approach was a gold-catalysed oxazole formation developed in our group

Introduction of a human- and keyboard-friendly N-glycan nomenclature

• Friedrich Altmann,
• Johannes Helm,
• Martin Pabst and
• Johannes Stadlmann

Beilstein J. Org. Chem. 2024, 20, 607–620, doi:10.3762/bjoc.20.53

• particular complex-type N-glycan structure found in human leukocytes [2]. A: SNFG depiction; B: IUPAC depictions; C: Oxford style; D: smart SNFG. Except for 1D, cartoons and codes were adapted from [3] (© GlyConnect v1.2.0, distributed under the terms of the Creative Commons Attribution 4.0 International

• showing the acronyms both with and without superscripts. Grey parts shall remind of the “hidden galactose” residue in the term “-4”. B: Structure N3.7.2B found in recombinant human erythropoietin [46]. The cartoon on the right side exemplifies the 4 sub-terms of the abbreviation and, again, the “hidden

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• investigations, accompanied by fermentation media optimization, of a newly isolated fungus, Penicillium shentong XL-F41, led to the isolation of twelve compounds. Among these are two novel indole terpene alkaloids, shentonins A and B (1 and 2), and a new fatty acid 3. Shentonin A (1) is distinguished by an

• enzymatic ring-expansion process in their respective fungi. Both shentonins A (1) and B (2) also feature a reduction of a carbonyl to a hydroxy group within the succinimide ring. All isolated compounds were subjected to antimicrobial evaluations, and compound 12 was found to have moderate inhibitory

• stimulating the production of a greater number of metabolite peaks, as shown in Figure 1. Scaled-up fermentation allowed us to isolate and characterize two new indole terpene alkaloids, shentonins A and B (1 and 2), a new fatty acid 3, and nine previously identified compounds 4–12, among which were gram

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

• Michael O. Akintubosun and
• Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

• Cloning, expression, and purification Streptomyces leeuwenhoekii NRRL B-24963 [28] was used as a template to amplify the hyg17 (GenBank CQR59633) with the primers 5’-GTTAGCCATATGACGGTCGCCGTCGTGGGC-3’ and 5’-GTAATGCTCGAGCGGCGCCACCGGCACCGA-3’. hyg17 was cloned into pTip-QC1 [10] using NdeI and XhoI

• inositols with NAD+, (b) myo-inositol with NAD+ or NADP, and (c) myo-inositol at different pH values (orange is HEPEs, green is Tris, blue is CHES, and red is CAPS). NAD(P)H concentrations were measured after 20 minutes. Michaelis–Menten plots for Hyg17 using varying concentrations of (d) myo-inositol, (e

• for inositol dehydrogenases. (b) Comparison of the hygromycin A (red) and hygromycin A-like (orange) biosynthetic gene clusters. A more detailed comparison can be found in Supporting Information File 1, Table S2. Kinetic parameters for Hyg17. Supporting Information Supporting Information File 36

Recent developments in the engineered biosynthesis of fungal meroterpenoids

• Zhiyang Quan and
• Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 578–588, doi:10.3762/bjoc.20.50

• , including the known antitumor compound subglutinol A (16) (Figure 3A and B) [17]. Among the novel compounds isolated from the production system, some exhibited intruiging pharmacological activities, such as antitumor (16), anti-HIV activity (17), and anti-Alzheimer's disease properties (18). Furthermore

• berkeleydione (28), respectively (Figure 5) [32][33]. In the initial reaction, AusE abstracts H-2 of 24, while PrhA abstracts H-5 of 24. PrhA and AusE form a double bond to yield preaustinoid A2 (25) and berkeleyone B (26), respectively (Figure 5). AusE abstracts H-5 of 25, forming a radical that initiates a

• ) derived from andiconin, can be converted into emervaridone B (33) and anditomin (34), respectively (Figure 6). Subsequently, 33 can be further modified into emervaridone C (35), which can be oxidized to 37 or 38 (Figure 6). In contrast, 34 is converted to compounds 36a and 36b (Figure 6). These multistep

Possible bi-stable structures of pyrenebutanoic acid-linked protein molecules adsorbed on graphene: theoretical study

• Yasuhiro Oishi,
• Motoharu Kitatani and
• Koichi Kusakabe

Beilstein J. Org. Chem. 2024, 20, 570–577, doi:10.3762/bjoc.20.49

• rotation at the alkyl chain (conformation II), as shown in Figure 1d. Rotational motion at the alkyl chain inevitably involves steric hindrance effects around the C–C bond. In particular, for motions corresponding to rotations around the C–C bond in PASE represented by the solid red line in Figure 1a and b

• , respectively. The solid, broken, and dotted red lines represent the rotation axis. Atomic geometry is visualized by Xcrysden [10] throughout this paper. (b) Schematic diagram of the dehydration-condensation structure of a hypothetical protein and PASE. Lys indicates lysine, and RC is the active center of the

• barrier top, and conformation 2 of PASE. (b) Relative energies of PASE in a vacuum are compared to those of reported values for PASE on graphene for each conformation [9]. The energy of conformation 1 is taken as an origin. Structure of PASE on graphene at the activation barrier top [9]. Detailed values

Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O–H insertion/base-promoted cyclization involving diazoarylidene succinimides

• Alexander Yanovich,
• Anastasia Vepreva,
• Ksenia Malkova,
• Grigory Kantin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 561–569, doi:10.3762/bjoc.20.48

• by the higher reactivity of benzyl bromide and the lower conformational mobility of the side chain with the ortho-phenylene link. As a result, new spirocyclic compounds 5 were obtained in high (5a,b) or moderate (5c) yields. With some other bromo-substituted OH substrates, we obtained O–H insertion

Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Irina V. Dubonosova,
• Olga Yu. Karlutova,
• Oleg P. Demidov,
• Alexander D. Dubonosov and
• Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

• Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don 344090, Russian Federation North Caucasus Federal University, Stavropol 355009, Russian Federation 10.3762/bjoc.20.47 Abstract A series of novel photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with

• sequential addition of Fe2+ and AcO−, we synthesized N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline substituent and studied the spectral-luminescent, photochromic and ionochromic properties. The phenanthroline moiety was incorporated into the molecule due to the

• catalysis and bioimaging [24][25][26]. In addition, such systems provide a convenient platform for creating chemo- and biosensors for rapid analysis of the ionic composition of the environment [27][28]. Results and Discussion The starting compound for the synthesis of N-acylated 2-(aminomethylene)benzo[b

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• , Bayer AG, Industriepark Höchst, 65926 Frankfurt am Main, Germany 10.3762/bjoc.20.46 Abstract The present work covers novel herbicidal lead structures that contain a 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine scaffold as structural key feature carrying a substituted phenyl side chain. These new compounds

• show good acyl-ACP thioesterase inhibition in line with strong herbicidal activity against commercially important weeds in broadacre crops, e.g., wheat and corn. The desired substituted 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines were prepared via an optimized BH3-mediated reduction involving tris

• -dihydro[1,3]thiazolo[4,5-b]pyridine; acyl-ACP thioesterase; bioisostere; herbicide; heterocycle; Introduction The presence of weed infestations exerts a high strain on food production around the globe by depleting resources for the crops and facilitating the transmission of diseases [1]. Although

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination

• Ruichen Lan,
• Brock Yager,
• Yoonsun Jee,
• Cynthia S. Day and
• Amanda C. Jones

Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43

• data plots; where not visible they are smaller than the icon for the data point. (a) Schematic for synthesis of [L–Au–L]SbF6 where L = JPhos. (b) Perspective drawing of the cation in crystalline [Au(P(C4H9)2(C12H9))2](SbF6)CH2Cl2 where P are represented by dotted spheres, Au atoms are represented by

• CH3OH reproduced in Figure 2, Table 3. (b) kobs for reaction of carbamate 1b (0.05 M) in DCM with catalyst 5 and titrated CH3OH/CD3OD. Error bars are from linear least squares analysis of raw data plots; where not visible they are smaller than the icon for the data point. Rate of urea 1a (0.05 M