The application of desymmetric enantioselective reduction of cyclic 1,3-dicarbonyl compounds in the total synthesis of terpenoid and alkaloid natural products

• Dong-Xing Tan and
• Fu-She Han

Beilstein J. Org. Chem. 2025, 21, 2085–2102, doi:10.3762/bjoc.21.164

• cyclic prochiral dicarbonyl substrates. In addition, various approaches could be used for the desymmetrization reactions such as enzyme catalytic-, organocatalyst-, and transition-metal-catalyzed reductions [5][6][7]. Advance about the synthesis of several terpenoid and alkaloid natural products (1–5

• -cyclopentanedione derivative was adopted as one of the key reactions, which facilitated the construction of the five-membered ring bearing an all-carbon quaternary center as the key chiral building block. Their synthesis began with 1,3-dione 40 (Scheme 2) [31][32], allylation of this substrate with allylic bromide

Multicomponent reactions IV

• Thomas J. J. Müller and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2082–2084, doi:10.3762/bjoc.21.163

• National Academy of Sciences of Ukraine, Nauky Av. 60, 61072 Kharkiv, Ukraine, Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody Sq. 4, 61077 Kharkiv, Ukraine 10.3762/bjoc.21.163 Keywords: multicomponent reactions; The synthesis of complex molecules is a cornerstone of modern

• optimization of promising lead structures has therefore inspired the development of powerful synthetic strategies. A glance at Web of Science reveals that one-pot methods and multicomponent reactions (MCRs) [1] have attracted steadily increasing attention within the scientific community over the past 25 years

• (Figure 1). According to a quick Web of Science [2] keyword search of "multicomponent reaction" and "one-pot reaction" (Figure 1A) and "multicomponent reaction" (Figure 1B) filtered by publication year, the impressive sum of 136,658 publications on multicomponent (Figure 1A) and one-pot reactions and

Discovery of cytotoxic indolo[1,2-c]quinazoline derivatives through scaffold-based design

• Daniil V. Khabarov,
• Valeria A. Litvinova,
• Lyubov G. Dezhenkova,
• Dmitry N. Kaluzhny,
• Alexander S. Tikhomirov and
• Andrey E. Shchekotikhin

Beilstein J. Org. Chem. 2025, 21, 2062–2071, doi:10.3762/bjoc.21.161

• )-one scaffold 1 was synthesized according to the optimized protocol developed by Bergman et al. [9]. Position 12 of indolo[1,2-c]quinazolin-6(5H)-one (1) (Scheme 1) corresponded to of the indole C3 position, which is typically used as a nucleophilic center for functionalization via reactions with

• introduce the carboxylic acid group a sequence of formylation/oxidation reactions was used. Vilsmeier–Haack reaction of 1 afforded 6-oxoindolo[1,2-c]quinazoline-12-carbaldehyde (2) (Scheme 1). All attempts to oxidize the aldehyde group of 2 to the corresponding carboxylic acid were hampered by the oxidative

Bioinspired total syntheses of natural products: a personal adventure

• Zhengyi Qin,
• Yuting Yang,
• Nuran Yan,
• Xinyu Liang,
• Zhiyu Zhang,
• Yaxuan Duan,
• Huilin Li and
• Xuegong She

Beilstein J. Org. Chem. 2025, 21, 2048–2061, doi:10.3762/bjoc.21.160

• capability have been increasing all the time by discovering and inventing a vast number of new organic reactions and methodologies [6]. However, could mankind become really stronger than Mother Nature one day? This question seems to have no answer as future is unpredictable. Maybe, Mother Nature could be our

• , monocerin and 12-hydroxymonocerin were presumably generated from their corresponding precursors through similar oxidation and oxa-Michael addition reactions. Given the fact that quinone methides served as a powerful platform for the development of rich useful organic transformations, especially, through

• underwent dehydroxylation protocol involving base-promoted mesylate elimination and catalytic hydrogenation reactions, providing 31a. Reduction of lactam and ester in one pot with LiAlH4 and acid-promoted hydrolysis of ketal protection to ketone furnished 32a. Finally, oxidation of the primary alcohol to

Switchable pathways of multicomponent heterocyclizations of 5-amino-1,2,4-triazoles with salicylaldehydes and pyruvic acid

• Yana I. Sakhno,
• Oleksander V. Buravov,
• Kostyantyn Yu. Yurkov,
• Anastasia Yu. Andryushchenko,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2030–2035, doi:10.3762/bjoc.21.158

• , 61072, Kharkiv, Ukraine Enamine Ltd., Winston Churchill Street 78, Kyiv 02094, Ukraine Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody sq., 4, 61022, Kharkiv, Ukraine 10.3762/bjoc.21.158 Abstract Switchable multicomponent reactions involving 3-substituted-5-amino-1,2,4

• -triazoles, pyruvic acid, and salicylaldehydes were studied under different conditions. Upon conventional heating, benzotriazolooxadiazocine-5-carboxylic acids were formed in the three-component reactions as single reaction products. Upon ultrasonic activation or mechanical stirring at room temperature, the

• multicomponent reaction of the same starting materials led to the formation of only tetrahydrotriazolopyrimidine derivatives. Keywords: 5-amino-1,2,4-triazole; heterocyclization; multicomponent reaction; salicylaldehyde; ultrasonication; Introduction Multicomponent reactions (MCRs) are a powerful tool for the

α-Ketoglutaric acid in Ugi reactions and Ugi/aza-Wittig tandem reactions

• Vladyslav O. Honcharov,
• Yana I. Sakhno,
• Olena H. Shvets,
• Vyacheslav E. Saraev,
• Svitlana V. Shishkina,
• Tetyana V. Shcherbakova and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2021–2029, doi:10.3762/bjoc.21.157

• ; quinoxalinone derivative; Ugi reaction; Introduction Multicomponent reactions are powerful tools in organic chemistry that enable the synthesis of structurally complex and multifunctional compounds from three or more starting materials in a single synthetic step. They are widely used in drug discovery because

• reactions, widely used as a green alternative for the synthesis of active pharmaceutical ingredients [7] and opens up the possibility of creating new compounds from the class of peptidomimetics [8][9][10], which often exhibit diverse biological effects [11] including antidiabetic [12], antiviral [13

• for the preparation of benzodiazepinone derivatives, which showed promising psychotropic effects [20][21][22][23][24], using a tandem combination of Ugi/azide–alkyne cycloaddition reactions. From this point of view, azido amines are promising reagents for use in the Ugi reaction, opening up the

Understanding the origin of stereoselectivity in the photochemical denitrogenation of 2,3-diazabicyclo[2.2.1]heptene and its derivatives with non-adiabatic molecular dynamics

• Leticia A. Gomes and
• Steven A. Lopez

Beilstein J. Org. Chem. 2025, 21, 2007–2020, doi:10.3762/bjoc.21.156

• Leticia A. Gomes Steven A. Lopez Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts, 02115, United States 10.3762/bjoc.21.156 Abstract Photochemical denitrogenation reactions of bicyclic azoalkanes produce strained bicyclic compounds of interest to

• synthetic organic chemists. We report a computational study on the mechanism of diazabicyclo[2.2.1]heptenes to address long standing mechanistic questions. Indeed, the mechanism of these reactions has been disputed for over six decades. We employed non-adiabatic molecular dynamics (NAMD) simulations

• ; stereoselectivity; Introduction Photochemical reactions utilize light as a sustainable energy source and are considered to be ‘green’ reactions [1][2]. Organic chromophores absorb light, accessing higher-lying excited state(s) that exhibit distinct reactivities, leading to bond breaking and formation, irreversibly

Measuring the stereogenic remoteness in non-central chirality: a stereocontrol connectivity index for asymmetric reactions

• Ivan Keng Wee On,
• Yu Kun Choo,
• Sambhav Baid and
• Ye Zhu

Beilstein J. Org. Chem. 2025, 21, 1995–2006, doi:10.3762/bjoc.21.155

• remained an intuitive and empirical practice, particularly for reactions that create non-central chirality. We put forward a stereocontrol connectivity index to parameterize asymmetric reactions according to the bond connectivity relationships between the prochiral stereogenic elements, the reactive sites

• , and the stereochemical-defining substituents. The indices can be generated based on analysis of the chemical structures of the starting materials and products, without mechanistic insights of the transformation. Representative examples of reactions that establish point chirality, axial chirality

• chiral molecules. Keywords: asymmetric reactions; axial chirality; catalysis; planar chirality; stereocontrol; Introduction Chirality is a ubiquitous and fundamental phenomenon in nature and thus holds an irreplaceable position in organic synthesis. At its most rudimental definition, chirality in a

Aryl iodane-induced cascade arylation–1,2-silyl shift–heterocyclization of propargylsilanes under copper catalysis

• Rasma Kroņkalne,
• Rūdolfs Beļaunieks,
• Armands Sebris,
• Anatoly Mishnev and
• Māris Turks

Beilstein J. Org. Chem. 2025, 21, 1984–1994, doi:10.3762/bjoc.21.154

• synthetic potential of iodane-mediated carbofunctionalization under copper catalysis. Keywords: arylation reactions; copper-catalysis; iodanes; propargylsilanes; 1,2-silyl shift; Introduction Highly electrophilic hypervalent iodine(III) reagents are considered as arene electrophilic synthons, making them

• the reagents of choice for arylation reactions, where an umpolung of reactivity is required [1]. Arylations employing diaryl-λ3-iodanes can be performed under metal-free [2] or metal-catalyzed conditions. For alkyne arylations [Cu] [3] or [Pd] catalysis [4][5][6] is typically employed. Internal

• analogs, that needed longer reaction times to reach full conversion (4 h for R = Ph, Me; 20 h for R = 3,5-(NO2)2C6H3). Conclusion In this work we have reported copper-catalyzed arylation reactions of propargylsilanes, using iodanes as the electrophilic aryl synthon equivalents. For internal nucleophile

Photochemical reduction of acylimidazolium salts

• Michael Jakob,
• Nick Bechler,
• Hassan Abdelwahab,
• Fabian Weber,
• Janos Wasternack,
• Leonardo Kleebauer,
• Jan P. Götze and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2025, 21, 1973–1983, doi:10.3762/bjoc.21.153

• reactions have been developed. Employing the simple amine, DIPEA, as the terminal reductant, products resulting from overall 2-electron or 4-electron-reduction processes could be obtained using either a photocatalytic approach under blue light irradiation or directly under UV-A light irradiation without an

• suitably electrophilic substrate at the carboxylic acid oxidation level provides an acylazolium species B, which typically reacts directly with nucleophiles or may first be transformed into the corresponding enolate derivative. Regardless of the individual pathway, NHC-catalyzed reactions of this type

• contrast to these numerous reports with carbon-based alkyl radicals, dual NHC/photoredox-mediated coupling processes between carboxylic acid derivatives and other classes of radical are lacking [22][23][24][25][26][27][28][29][30]. In particular, to the best of our knowledge, formal reduction reactions of

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

• -catalyzed acylation, and local desymmetrization. In this review, we cover total syntheses that utilize enantioselective desymmetrization of prochiral 1,3-diols. Review Desymmetrization via enzymatic acylation Enzymatic reactions represent one of the most useful tools in total synthesis. Through combination

• with organic reactions, this chemo-enzymatic strategy has been successfully utilized in the synthesis of complex molecules [22][23]. Enzymatic reactions feature a convenient operation due to their relative insensitivity to water and oxygen, as well as a specificity to certain substrates, resulting in

• (125) was obtained through a 12-step sequence from 124. Desymmetrization via transition-metal-catalyzed acylation Although enzymatic acylation reactions are widely employed in total synthesis, certain substrates are incompatible with acylation catalyzed by existing lipases. Inspired by enzymatic

Rhodium-catalysed connective synthesis of diverse reactive probes bearing S(VI) electrophilic warheads

• Scott Rice,
• Julian Chesti,
• William R. T. Mosedale,
• Megan H. Wright,
• Stephen P. Marsden,
• Terry K. Smith and
• Adam Nelson

Beilstein J. Org. Chem. 2025, 21, 1924–1931, doi:10.3762/bjoc.21.150

• amino acids [8][9][10]. Sets of reactive probes are generally prepared using robust reactions, most usually amide formation, chosen from the toolkit that currently dominates medicinal chemistry [11] which may, in turn, limit probe structural diversity. We have developed a unified connective approach for

• the reactive probes would be prepared by dirhodium-catalysed reactions between pairs of building blocks: an α-diazoamide 2 bearing a S(VI) electrophile and a suitable co-substrate (→ 3) (Figure 1). Here, metal-catalysed carbenoid chemistry was chosen because of the wide range of potentially reactive

• with, we investigated reactions of the α-diazoamide substrates D1, D2 and D3 with the 16 co-substrates C1–16 catalysed by three diverse [21] dirhodium catalysts (Rh2piv4, Rh2pfb4 and Rh2cap4) i.e., an array of 144 reactions. An α-diazoamide substrate (20 μmol; 16 μL of a 1.25 M solution in CH2Cl2) and

Synthesis, biological and electrochemical evaluation of glycidyl esters of phosphorus acids as potential anticancer drugs

• Almaz A. Zagidullin,
• Emil R. Bulatov,
• Mikhail N. Khrizanforov,
• Damir R. Davletshin,
• Elvina M. Gilyazova,
• Ivan A. Strelkov and
• Vasily A. Miluykov

Beilstein J. Org. Chem. 2025, 21, 1909–1916, doi:10.3762/bjoc.21.148

• . Experimental General. All reactions and manipulations were carried out under dry pure N2 in standard Schlenk apparatus. All solvents were distilled from sodium/benzophenone or phosphorus pentoxide and stored under nitrogen before use. The NMR spectra were recorded on a Bruker MSL-400 (1H 400 MHz, 31P 161.7 MHz

Stereoselective electrochemical intramolecular imino-pinacol reaction: a straightforward entry to enantiopure piperazines

• Margherita Gazzotti,
• Fabrizio Medici,
• Valerio Chiroli,
• Laura Raimondi,
• Sergio Rossi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2025, 21, 1897–1908, doi:10.3762/bjoc.21.147

• conditions, the continuous process afforded higher productivities and space-time yields than the batch reactions due to a short residence time. This work provides a mild, efficient, and scalable alternative to traditional methods for the synthesis of tetrasubstituted enantiopure piperazines, with potential

• photochemical and electrochemical methods, have been explored. Over the past two decades a variety of light-promoted imino-pinacol coupling reactions have been developed, involving the use of catalytic transition-metal complexes [35][36], organic dyes [37][38][39], and polyaromatic compounds [40][41] as

• /cm2), total charge 2.2 F/mol, dry DMF (0.125 M). Yields reported are isolated yields. Reactions were performed on a 0.5 mmol scale. Continuous flow synthesis of piperazine 2a. The yield was determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as internal standard. Reactions were performed

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

• -containing compounds makes use of intramolecular 1,3-dipolar cycloaddition reactions [15], including examples with nitrone ylides [16][17][18][19][20][21][22]. Our research group has exploited this approach for the synthesis of alkaloids such as myrioxazine A and aspidospermidine [23][24]. With a nitrone 1,3

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

• asymmetric Mannich reactions, the past two decades have witnessed the remarkable evolution of CPA catalysis into one of the most versatile platforms for achieving diverse enantioselective transformations [3][4][5][6][7][8]. CPA catalysts are generally recognized as bifunctional catalysts with two distinct

• effects of the CPAs, which establish a chiral microenvironment within the chiral scaffold that governs the stereoselectivity of asymmetric reactions. Chiral molecules, characterized as three-dimensional structures that are nonsuperimposable with their mirror image, have significant applications in

• asymmetric catalytic reactions to synthesize chiral molecules with stereogenic centers has been developed. Moreover, the rapid advancement of axially chiral molecules in asymmetric synthesis has been made possible by employing CPA catalysis, notably pioneered by Akiyama [10], Tan [11] and others. However

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

• efficiency. Keywords: metal-organic frameworks; post-synthesis modification; supramolecular catalysis; Introduction Most enzymatic reactions take place in multifunctional cavities in which multiple amino acid residues work cooperatively to orient and activate reactants [1][2][3]. These residues may also

• by increasing the binding affinity for the lipophilic reactants and by decreasing the energy required to desolvate acid/base amino acid catalysts [34][35]. Lipophilicity has also been found to be beneficial in condensation reactions as the removed water molecules are repelled by the hydrophobic

• of the MOF product digested in D2SO4/DMSO-d6 (Figure 2B). Conversions were estimated by selecting the “same” proton in the starting material and in the products and integrating the corresponding peaks and setting the total to 100% (see Supporting Information File 1). We observed that the reactions

Photoswitches beyond azobenzene: a beginner’s guide

• Michela Marcon,
• Christoph Haag and
• Burkhard König

Beilstein J. Org. Chem. 2025, 21, 1808–1853, doi:10.3762/bjoc.21.143

• forward and backward isomerisation can occur simultaneously. Moreover, some unwanted photochemical side reactions ΦS can occur, as shown in the Equation 4: A is one state of the photoswitch, B the second state, and B’ a generic degradation product. Fatigue resistance measures how many times the

• photoswitch can be switched before it is degraded by side reactions. It is typically reported as cyclability Z50, which “is the number of cycles required to reduce the initial absorbance at a specific wavelength by 50%” [3]. The quantum yield ΦS of these side reactions determines the resistance to fatigue of

• the photoswitch. Examples of photogenerated side reactions can be oxidation or irreversible rearrangements. In the following sections, seven classes of photoswitches beyond the classic azobenzene are introduced and discussed (Scheme 1). Each of them shows unique photophysical behaviour and has

Fe-catalyzed efficient synthesis of 2,4- and 4-substituted quinolines via C(sp²)–C(sp²) bond scission of styrenes

• Prafull A. Jagtap,
• Manish M. Petkar,
• Vaishnavi R. Sawant and
• Bhalchandra M. Bhanage

Beilstein J. Org. Chem. 2025, 21, 1799–1807, doi:10.3762/bjoc.21.142

• strategies have been explored in recent decades for the synthesis of structurally diverse quinolines. Among them, transition-metal-catalyzed multicomponent reactions (MCRs) have emerged as particularly effective for constructing complex quinoline-based heterocycles [26][27][28]. Catalytic pathways such as

• cycloaddition, tandem annulation, intramolecular cyclization, and cross-coupling reactions are commonly employed under thermal conditions, utilizing metal catalysts based on Pd, Ru, Au, Cu, and Fe to access a wide array of substituted quinoline frameworks [29][30][31][32][33][34][35][36][37][38]. Conversely, in

[3 + 2] Cycloaddition of thioformylium methylide with various arylidene-azolones in the synthesis of 7-thia-3-azaspiro[4.4]nonan-4-ones

• Daniil I. Rudik,
• Irina V. Tiushina,
• Anatoly I. Sokolov,
• Alexander Yu. Smirnov,
• Alexander R. Romanenko,
• Alexander A. Korlyukov,
• Andrey A. Mikhaylov and
• Mikhail S. Baranov

Beilstein J. Org. Chem. 2025, 21, 1791–1798, doi:10.3762/bjoc.21.141

• -membered heterocyclic ring are of particular interest, since they exhibit a wide range of pharmacological activity (Scheme 1) [6][7][8][9][10][11]. The most straightforward and powerful methods of such substance’s syntheses are based on cycloaddition reactions [12][13][14][15]. Previously, we and other

Synthesis of chiral cyclohexane-linked bisimidazolines

• Changmeng Xi,
• Qingshan Sun and
• Jiaxi Xu

Beilstein J. Org. Chem. 2025, 21, 1786–1790, doi:10.3762/bjoc.21.140

• alcohols and utilized in different metal-catalyzed asymmetric organic reactions [1][2][3][4][5][6][7][8][9]. In comparison with bisoxazoline ligands, relatively less attention has been paid to bisimidazoline ligands [10][11][12][13][14][15]. Some well investigated bisimidazoline ligands are pyridine-linked

• bisimidazoline (PyBim) ligands derived from pyridine-2,6-dicarbonitrile or pyridine-2,6-dicarboxylic acid and vicinal diamines, as analogues of pyridine-linked bisoxazoline (PyBOX) ligands [16][17]. They exhibited excellent performance in metal-catalyzed asymmetric organic reactions. Chiral rigid backbone-linked

• bisoxazoline ligands, such as anthracene-1,8-linked bisoxazolines (AnBOX) [18][19][20] showed excellent enantioselectivities for certain substrates due to their ability to fix transition states in asymmetric reactions, realizing excellent stereoselectivities. However, they also presented some limitations to

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

• processes. For example, supramolecular self-assembly technology enhances the targeting of chemotherapeutic drugs to tumor tissues, reducing systemic adverse reactions. (3) Macrocyclic aromatic supramolecular nano-valves have a pseudo-rotaxane structure with host–guest coordination and the kinetic properties

• a series of neatly arranged hydrophilic phenolic hydroxy groups that can be selectively modified through chemical reactions [49]. CAs feature large hydrophobic cavities whose size can be precisely modulated by varying the number of aromatic rings. This structural tunability enables the cavities of

• modifiable ring positions, and many PA derivatives with different functional groups can be obtained through the cyclization reaction of 1,4-dialkoxybenzene monomers or post-synthetic modification reactions [74]. PAs possess a unique internal cavity characterized by an electron-rich and hydrophobic

Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

• Mai Uchibori,
• Nanami Murate,
• Kanako Shima,
• Tatsunori Sakagami,
• Ko Kanehisa,
• Gary James Richards,
• Akiko Hori and
• Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756, doi:10.3762/bjoc.21.138

• ; single crystals; thiones; Introduction In the past several years, C–N atropisomers (C–N axially chiral compounds) owing to the rotational restriction around a C–N single bond have received great attention as new target molecules for catalytic asymmetric reactions. Highly enantioselective syntheses of

Thermodynamics and polarity-driven properties of fluorinated cyclopropanes

• Matheus P. Freitas

Beilstein J. Org. Chem. 2025, 21, 1742–1747, doi:10.3762/bjoc.21.137

• to modulate properties that enhance the performance of pharmaceuticals and materials. This quantum-chemical study explores the energetic implications of fluorinating cyclopropane, providing insights into molecular characteristics arising from the polar C–F bond. Isodesmic reactions revealed that the

• reactants and products [15]. While such reactions are theoretically possible, they are not always experimentally feasible. Their primary purpose is to provide insight into the favorability of specific processes. In this study, we employ the following isodesmic reaction to assess whether the fluorination of

• substitution is endothermic and, therefore, destabilizing [8]. This destabilization was attributed to the greater s-character of the orbital involved in bonding to the substituent. In contrast, our calculations at the B3LYP-GD3BJ/6-311++G(d,p) level revealed that the reactions leading to the fluorinated

Preparation of a furfural-derived enantioenriched vinyloxazoline building block and exploring its reactivity

• Madara Darzina,
• Anna Lielpetere and
• Aigars Jirgensons

Beilstein J. Org. Chem. 2025, 21, 1737–1741, doi:10.3762/bjoc.21.136

• reactions. Out of these, the aza-Diels–Alder reaction with TsNCO was successful, leading to a highly diastereoselective formation of an oxazolo[3,2-c]pyrimidine derivative. Keywords: aza-Diels–Alder reaction; electrosynthesis; furfural; valinol; vinyloxazoline; Introduction The utilization of biomass as