Search results

Search for "regioselective" in Full Text gives 554 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

  • Betty A. Kustiana,
  • Galuh Widiyarti and
  • Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

Graphical Abstract
PDF
Album
Review
Published 28 May 2025

Recent total synthesis of natural products leveraging a strategy of enamide cyclization

  • Chun-Yu Mi,
  • Jia-Yuan Zhai and
  • Xiao-Ming Zhang

Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81

Graphical Abstract
  • a regioselective manner. From tetracyclic compound 11, a one-pot facial and regioselective hydroboration/amide reduction followed by oxidation produced (+)-lycoposerramine Q, which was then converted to (+)-fawcettidine by Ley oxidation. Alternatively, hydroboration of 11 in mild conditions without
  • triggered a Grob fragmentation process of hemiaminal 16 and afforded the imide compound 17. Final regioselective reduction of one of the two carbonyls on the imide completed the synthesis of (−)-phlegmariurine B. Annulation Total syntheses of cephalotaxine and cephalezomine H The [2 + 3] annulation of
  • cyclopentane ring, dihydroxylation, and oxidation of the diol to a diketone, produced intermediate 25 in its enol form. From this common intermediate, regioselective etherification at the less hindered position formed an enol ether. Final reduction of both the amide and the ketone using alane completed the
PDF
Album
Review
Published 22 May 2025

Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

  • Shyam Sathyamoorthi,
  • Appasaheb K. Nirpal,
  • Dnyaneshwar A. Gorve and
  • Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954, doi:10.3762/bjoc.21.78

Graphical Abstract
  • regioselective, diastereoselective, and metal-free protocol for alkene amino-hydroxylation, which compared favorably to prior art in this area [25][26][27][28][29][30][31][32]. Naturally, we wondered if other O-nucleophiles were competent in the ring-opening of the aziridinium intermediate. Indeed, almost all
PDF
Album
Supp Info
Full Research Paper
Published 19 May 2025

A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids

  • Zhiyang Zhang,
  • Jialei Hu,
  • Hanfeng Ding,
  • Li Zhang and
  • Peirong Rao

Beilstein J. Org. Chem. 2025, 21, 926–934, doi:10.3762/bjoc.21.75

Graphical Abstract
  • molecules could be synthesized from diol 9 through a late-stage modification involving adjustment of the oxidation state and regioselective acylation. The formation of 9 was envisioned to proceed via an intramolecular pinacol coupling [30][31] of [5,5,6,6]-tetracycle 10, which forges the A2 ring while
PDF
Album
Supp Info
Full Research Paper
Published 12 May 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

Graphical Abstract
  • , thereby offering unprecedented control over chemo-, regio-, and stereoselectivity parameters in catalytic manifolds. In 2015, the Jiang group developed a palladium-catalyzed regioselective three-component C1 insertion reaction (Scheme 1) [19]. In this reaction, an o-iodoaniline 1, phenylacetylene, and
  • in steering catalytic selectivity. In 2016, the Jiang group achieved regioselective control in the gold-catalyzed intramolecular hydroarylation of alkynes by modulating the electronic and steric effects of ligands (Scheme 2) [20]. Mechanistically, the electron-deficient phosphite ligand L1 and the
  • ligand-controlled regioselective migratory insertion process, reaction of Int-21 and Int-22 leads to the formation of π-allylpalladium intermediates Int-23 or Int-24, depending on the ligand employed. Finally, cyclization of Int-23 or Int-24 yields the tricyclic product 13 or the tetracyclic product 14
PDF
Album
Review
Published 07 May 2025

Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes

  • Patricia Gómez-Roibás,
  • Andrea Chaves-Pouso and
  • Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71

Graphical Abstract
  • mechanism for the copper-catalyzed diastereoselective dimerization of 4,4-dichoro-2-butenoic acid derivatives (Scheme 4). Initially, the LCu–pin complex generated through reaction between LCu–Ot-Bu and B2pin2 undergoes coordination and regioselective insertion into 1 giving rise to β-borylated organocopper
PDF
Album
Supp Info
Letter
Published 05 May 2025

Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers

  • Seeun Lim,
  • Teresa Kim and
  • Yunmi Lee

Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63

Graphical Abstract
  • cyanating reagents, such as p-toluenesulfonyl cyanide (TsCN) and N-cyano-N-phenyl-p-toluenesulfonamide [29]. The hydroboration of allenes with 9-BBN (9-borabicyclo[3.3.1]nonane) as the hydride source, followed by regioselective cyanation with allylic boranes, provided nitrile-substituted quaternary carbon
  • -catalyzed regioselective hydroalumination of allenes using diisobutylaluminum hydride (DIBAL-H), we envisioned that the nucleophilic attack of allylaluminum reagents on electrophilic cyanating reagents could provide a regioselective pathway for the synthesis of alkyl nitriles bearing quaternary carbon
  • involves the regioselective nucleophilic attack of allylaluminum C on tosyl cyanide, which proceeds at the γ-position via six-membered ring transition state D, leading to the formation of the desired nitrile product. Transition state D is responsible for the E-selectivity observed in trisubstituted allenes
PDF
Album
Supp Info
Full Research Paper
Published 17 Apr 2025

Recent advances in allylation of chiral secondary alkylcopper species

  • Minjae Kim,
  • Gwanggyun Kim,
  • Doyoon Kim,
  • Jun Hee Lee and
  • Seung Hwan Cho

Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51

Graphical Abstract
  • into a powerful and versatile tool in asymmetric synthesis, capable of employing a wide array of organometallic reagents that furnish the desired compounds with high efficiency and selectivity. The regioselective asymmetric construction of stereogenic carbon centers from prochiral allylic substrates
  • metathesis with HBpin to afford a vinylboronic ester intermediate 45 alongside the regenerated L*CuH catalyst, completing the first catalytic cycle. Subsequently, a ligand-controlled regioselective migratory insertion of L*CuH into the vinylboronic ester 18 delivers the corresponding chiral alkylcopper
  • with olefins bearing electronic directing groups (such as aryl, boryl, or trifluoromethyl substituents) that guide regioselective hydrocupration, unactivated alkyl-substituted alkenes pose a persistent challenge. The recent breakthrough in CuH-catalyzed enantioselective and diastereoselective allylic
PDF
Album
Review
Published 20 Mar 2025

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

Graphical Abstract
  • reacts with the enolate of the ketone, which is stabilized by coordination with Fe(III), resulting in the formation of the C–C bond. A further oxidative aromatization process affords compound I. Compared to the protocol developed by Zhang et al. [24], the reaction is less regioselective, as Troger’s base
  • in the case of formaldehyde, making the reaction more regioselective. In the cases shown above, we discussed different ways to activate DMSO. In almost all of them, MMS appears as the reactive species due to its high electrophilicity, which allows for an efficient nucleophilic addition, and the
PDF
Album
Review
Published 13 Mar 2025

Vinylogous functionalization of 4-alkylidene-5-aminopyrazoles with methyl trifluoropyruvates

  • Judit Hostalet-Romero,
  • Laura Carceller-Ferrer,
  • Gonzalo Blay,
  • Amparo Sanz-Marco,
  • José R. Pedro and
  • Carlos Vila

Beilstein J. Org. Chem. 2025, 21, 533–540, doi:10.3762/bjoc.21.41

Graphical Abstract
  • on the regioselective electrophilic functionalization of this nitrogen heterocycle [15][16][17][18][19][20][21][22][23][24][25]. However, the vinylogous functionalization of 5-aminopyrazoles has not been described to the best of our knowledge (Figure 2). As a part of our ongoing interest in the
  • functionalization of 5-aminopyrazoles [26], we decided to study 4-alkenyl-5-aminopyrazoles as nucleophiles in the vinylogous addition reaction to electrophiles. Herein, we report the regioselective and diastereoselective functionalization of 4-cyclohexenyl-5-aminopyrazoles using alkyl trifluoropyruvates [27][28][29
  • yield decreased, possibly due to the formation of imine B, which might be favored by the dehydration effect of the molecular sieves. Conclusion In summary, a regioselective and diastereoselective vinylogous addition reaction of 4-alkenyl-5-aminopyrazoles to alkyl trifluoropyruvate has been studied
PDF
Album
Supp Info
Letter
Published 10 Mar 2025

Electrochemical synthesis of cyclic biaryl λ3-bromanes from 2,2’-dibromobiphenyls

  • Andrejs Savkins and
  • Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

Graphical Abstract
  • diaryl λ3-bromanes under remarkably mild conditions with subsequent applications of the in situ-generated arynes in cycloaddition reactions [3], meta-selective reactions with oxygen and nitrogen nucleophiles [4][5], regiodivergent meta or ortho-alkynylations [6], and regioselective (di)halogenation [7
PDF
Album
Supp Info
Letter
Published 27 Feb 2025

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

  • Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

Graphical Abstract
  • groups) with little [73], if any, transition-state binding [36][80][81]. Thus, these macrocycles depend on the catalytic concept of organization; polarization is a minor contributor. Size-exclusion and regioselective outcomes are possible [56][82][83][84][85], and symmetric arrays of chiral units (like
PDF
Album
Supp Info
Perspective
Published 24 Feb 2025

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

  • Rituparna Das and
  • Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

Graphical Abstract
  • sections. Similarly, Pertel and co-workers also demonstrated the use of 2-(2,2,2-trichloroethoxy)-2-oxazoline glycosyl donor 22 (Scheme 4) which could be used for stereo- and regioselective glycosylations using extremely mild conditions [94] and requiring low concentrations of the catalyst. In this case
  • the regioselective glycosylation produced products 24:25 in a 4:1 ratio in 61% yield. Aglycon transfer was also observed in the reaction producing 26 in 15% yield. The predominance of product 24 also indicates towards a higher nucleophilicity of the C-4 position of the glucoside acceptor 26
PDF
Album
Review
Published 17 Feb 2025

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

  • Asahi Kanno,
  • Ryo Tanifuji,
  • Satoshi Yoshida,
  • Sota Sato,
  • Saori Maki-Yonekura,
  • Kiyofumi Takaba,
  • Jungmin Kang,
  • Kensuke Tono,
  • Koji Yonekura and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

Graphical Abstract
  • reaction involves an in situ generation of the iminium cation A followed by isomerization to the thermodynamically more stable iminium cation B. Subsequent nucleophilic attack of a copper acetylide enabled regioselective C–C bond formation at the C11 position. After removal of the cyclic acetal, the
PDF
Album
Supp Info
Letter
Published 28 Jan 2025

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

  • Seungmin Lee,
  • Minsuk Kim,
  • Hyewon Han and
  • Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

Graphical Abstract
  • amidation process of dioxazolones. Dioxazolone 1 binds to the chiral copper complex 3, generating the adduct INT-1. Decarboxylation then occurs, forming the copper nitrenoid intermediate INT-2, subsequently undergoing hydrogen atom transfer in a regioselective manner to afford INT-3. The related acyl
  • dioxazolone bearing a linear alkyl group was efficiently converted to the N-vinylamide 26a in good yield. The observed regioselectivity followed the anti-Markovnikov fashion stemming from the regioselective hydrozirconation of the alkyne using Schwartz’s reagent [100]. Aryl substituents on the dioxazolone
PDF
Album
Review
Published 22 Jan 2025

Cu(OTf)2-catalyzed multicomponent reactions

  • Sara Colombo,
  • Camilla Loro,
  • Egle M. Beccalli,
  • Gianluigi Broggini and
  • Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

Graphical Abstract
  • directly to the alkene, then reacts with the nucleophile to afford product 7. The regioselective 1,2-difunctionalization of allyl alcohol has been developed as a three-component cascade reaction using arenes and sulfonamides as nucleophiles to achieve arylation/hydroamination processes. The reaction
  • Biginelli reaction was carried out starting from salicylaldehyde providing hydroxyphenyl-substituted dihydropyrimidines 18 [30]. Subsequently, the regioselective oxidation of the dihydropyrimidine ring in the presence of CAN allowed the formation of new pyrimidinone derivatives 19. The efficacy of Cu(OTf)2
  • dihydropyrimidines 18. Regioselective synthesis of 1,4-dihydropyridines 20. Synthesis of tetrahydropyridines 21. Synthesis of furoquinoxalines 22. Synthesis of 2,4-substituted quinolines 23. Synthesis of cyclic ether-fused tetrahydroquinolines 24. Practical route for 1,2-dihydroisoquinolines 25. Synthesis of 2,3
PDF
Album
Review
Published 14 Jan 2025

Recent advances in organocatalytic atroposelective reactions

  • Henrich Szabados and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

Graphical Abstract
  • of the developed protocol was demonstrated on a gram-scale reaction, where the corresponding product 200 was obtained with an acceptable decrease of yield and enantioselectivity (65%, 94% ee). Mechanistically, a chemo- and regioselective nucleophilic addition followed by dehydration leads to diimine
PDF
Album
Review
Published 09 Jan 2025

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

  • Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

Graphical Abstract
  • centrifugation. In the same way as a calix[4]pyrrole was used as organocatalyst for cyclic carbonate synthesis from epoxide and CO2, as discussed in section 1.1, Gallo and co-workers investigated the organocatalytic activity of porphyrin/TBACl binary catalytic systems for the regioselective cycloaddition of CO2
PDF
Album
Review
Published 27 Nov 2024

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

  • Ritu Mamgain,
  • Kokila Sakthivel and
  • Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

Graphical Abstract
  • group from position 4, and then regioselective vicinal functionalization of the generated aryne. The method's compatibility with halide-substituted aryl compounds enhances its versatility and practicality. Moreover, the completion of reaction within a mere 40 minutes at room temperature underscores its
  • easily recycled just by washing it with ethanol, retaining its catalytic activity for arylation up to three cycles without any compromise. Thus, this procedure could be considered economic as well as environment-friendly. In 2019, Kalek and co-workers reported the regioselective C–H arylation of 2
  • approach providing regioselective access to N2-arylated products along with high yields. The synthetic route could also be applied for the synthesis of N2-arylbenzotriazoles which are promising scaffolds for pharmaceuticals. Subsequently, the impact of the aryl group present in the diaryl iodonium salts on
PDF
Album
Review
Published 13 Nov 2024

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

Graphical Abstract
  • -galactose and subsequent perbenzoylation afforded an anomeric mixture (α:β = 87:13) of tribenzoyl-4,6-benzylidene-ᴅ-galactose from which the pure α-anomer 10a was separated (Scheme 6) [20]. Cleavage of the acetal and subsequent regioselective replacement of the hydroxy group OH-6 with an iodide by
PDF
Album
Review
Published 08 Nov 2024

Copper-catalyzed yne-allylic substitutions: concept and recent developments

  • Shuang Yang and
  • Xinqiang Fang

Beilstein J. Org. Chem. 2024, 20, 2739–2775, doi:10.3762/bjoc.20.232

Graphical Abstract
  • precise and highly regioselective construction of an array of novel chiral coumarin derivatives, characterized by their exceptional synthetic efficiency and remarkable tolerance towards a broad spectrum of functional groups (Scheme 21, 22a–n). Almost at the same time, Lin et al. [71] also devised a copper
PDF
Album
Review
Published 31 Oct 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Graphical Abstract
  • amination: Direct and selective CH-aminations and amidations are challenging reactions. In this context, the regioselective sulfonamidation of (hetero)aromatic groups was achieved by the Lei group via dehydrogenative aryl C–H/N–H cross-coupling [9]. A crucial step in this transformation is the generation of
  • method for the regioselective thiolation of aromatic C–H bonds by activating the thiol rather than the arene [19]. For their developed reaction, Pt electrodes were used in an undivided cell with a mixture of HFIP/DCE 3:1 at room temperature under argon. Late-stage functionalization was demonstrated for
PDF
Album
Review
Published 09 Oct 2024

Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams

  • Valentina Giraldi,
  • Giandomenico Magagnano,
  • Daria Giacomini,
  • Pier Giorgio Cozzi and
  • Andrea Gualandi

Beilstein J. Org. Chem. 2024, 20, 2461–2468, doi:10.3762/bjoc.20.210

Graphical Abstract
  • . Across all tested substrates, nucleophilic attack predominantly occurred at the homobenzylic position, leading to the regioselective formation of clavam derivative with 2-benzylic substitution due to aryl stabilization of the radical intermediate (see mechanistic discussion below). We briefly
PDF
Album
Supp Info
Full Research Paper
Published 01 Oct 2024

Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles

  • Yutaro Miyashita,
  • Sae Someya,
  • Tomoko Kawasaki-Takasuka,
  • Tomohiro Agou and
  • Takashi Yamazaki

Beilstein J. Org. Chem. 2024, 20, 2421–2433, doi:10.3762/bjoc.20.206

Graphical Abstract
  • -to-handle reagent, NaOCl·5H2O. Because very little has been disclosed about the reactivity of such 2,3-epoxyesters, their epoxy ring opening by a variety of nucleophiles was carried out and we succeeded in clarifying these chemo- as well as regioselective processes proceeding via the SN2 mechanism to
  • failed in this transformation and recovery of 2b was observed (Table 2, entry 10). As was pointed out in the introductory section, the highly regioselective epoxy ring opening is well compared with the case when the nonfluorinated substrate (Ph instead of CF3 in 2b) was employed [25][26]. With the
PDF
Album
Supp Info
Full Research Paper
Published 25 Sep 2024

Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents

  • Naoki Takeda,
  • Shuichi Akasaka,
  • Susumu Kawauchi and
  • Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2024, 20, 2234–2241, doi:10.3762/bjoc.20.191

Graphical Abstract
  • the field of bioconjugation and materials research. We previously reported a regioselective double addition of organic azides to octadehydrodibenzo[12]annulene derivatives with electron-rich alkyloxy substituents. In order to increase the reaction rate, electron-withdrawing substituents were
  • introduced into octadehydrodibenzo[12]annulene. In this report, the synthesis of new octadehydrodibenzo[12]annulene derivatives, regioselective double addition of organic azides, and an application to crosslinking polymers are described. Keywords: annulene; click chemistry; polymerization; strain-promoted
  • ], and crosslinked polymers [14][15][16][17]. Since crosslinking polymers requires high reaction efficiency under mild conditions, developing such reactions is crucial. We previously reported the regioselective double azide addition to octadehydrodibenzo[12]annulene with hexyloxy substituents (DBA-OHex
PDF
Album
Supp Info
Full Research Paper
Published 04 Sep 2024
Other Beilstein-Institut Open Science Activities