Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

• James Guevara-Pulido,
• Fernando González-Pérez,
• José M. Andrés and
• Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

• yields [27]. These reactions have been utilized in the enantioselective synthesis of aryl sulfoxides through the arylation of sulfonate anions in the presence of palladium catalysts [28][29]. They have also been used in the synthesis of the neuraminidase inhibitor (−)-oseltamivir [30] and the

• enantiocontrol [34][35][36][37][38][39]. In our studies on the organocatalytic enantioselective synthesis of 1,5-ketoaldehydes [40], we found that the prolinol derivative A is an outstanding catalyst for the enantioselective preparation of these adducts (Scheme 2). We are currently investigating whether this

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

• area of medicinal chemistry [93][94][95][96][97]. In 2018, Buchwald and co-workers unveiled the enantioselective synthesis of benzylic amines through the asymmetric Markovnikov hydroamidation of alkenes utilizing diphenylsilane in copper catalysis under mild reaction conditions [98]. Dioxazolones, as

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

• -dihydroquinazolin-4(1H)-one derivatives 26. Synthesis of polysubstituted pyrroles 27. Enantioselective synthesis of polysubstituted pyrrolidines 30 directed by the copper complex 29. Synthesis of 4,5-dihydropyrazoles 31. Synthesis of 2 arylisoindolinones 32. Synthesis of imidazo[1,2-a]pyridines 33. Synthesis of

Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction

• Yuta Kabumoto,
• Eiichiro Yoshimoto,
• Bing Xiaohuan,
• Masato Morita,
• Motohiro Yasui,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2024, 20, 2776–2783, doi:10.3762/bjoc.20.233

• reports on the preparation of chiral molecules possessing a tetrafluoroethylene unit on an asymmetric carbon center in a high optical purity, and to the best of our knowledge, only the following have been published so far (Scheme 1). As a highly enantioselective synthesis, there has been a pioneering work

5th International Symposium on Synthesis and Catalysis (ISySyCat2023)

• Anthony J. Burke and
• Elisabete P. Carreiro

Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227

• organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen”, an interesting approach to recycling the very useful cinchona squaramide organocatalysts was described. This approach involved functionalization of the organocatalyst with a lipophilic linker (octadecyl side chains), resulting in a

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

Asymmetric organocatalytic synthesis of chiral homoallylic amines

• Nikolay S. Kondratyev and
• Andrei V. Malkov

Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201

• concerted SN2-key intermediate 60 must be at least 18.9 kcal/mol more favoured than a separated imine–chloride ion pair 61 attacked by the free allylsilane (Figure 3). Altogether, the developed methodology can be formally viewed as a useful tool for the enantioselective synthesis of chiral α-carboxyl-2,3

Primary amine-catalyzed enantioselective 1,4-Michael addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones

• Pooja Goyal,
• Akhil K. Dubey,
• Raghunath Chowdhury and
• Amey Wadawale

Beilstein J. Org. Chem. 2024, 20, 1518–1526, doi:10.3762/bjoc.20.136

• (Scheme 2) were obtained in good to excellent yields (71–97%) and enantioselectivities (83.5–98% ee). Molecules containing two or more biologically relevant heterocycle motifs are receiving attention in drug discovery research [31][32][33]. The enantioselective synthesis of such hybrid molecules is

Synthetic applications of the Cannizzaro reaction

• Bhaskar Chatterjee,
• Dhananjoy Mondal and
• Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

• -β-lactone core 73 (Scheme 21). An expedient use of the Cannizzaro reaction was exemplified in the noteworthy enantioselective synthesis towards the indole alkaloids 16-epivellosimine, (+)-polyneuridine, and (+)-macusine A as reported by Cook and coworkers [89]. This was effectively worked out from ᴅ

Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck–Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles

• Arnaldo G. de Oliveira Jr.,
• Martí F. Wang,
• Rafaela C. Carmona,
• Danilo M. Lustosa,
• Sergei A. Gorbatov and
• Carlos R. D. Correia

Beilstein J. Org. Chem. 2024, 20, 940–949, doi:10.3762/bjoc.20.84

Chiral phosphoric acid-catalyzed transfer hydrogenation of 3,3-difluoro-3H-indoles

• Yumei Wang,
• Guangzhu Wang,
• Yanping Zhu and
• Kaiwu Dong

Beilstein J. Org. Chem. 2024, 20, 205–211, doi:10.3762/bjoc.20.20

• isostere of polar functional groups [5][6]. Chiral indoline is an important member of the class of nitrogen-containing heterocyclic compounds that often exhibits various pharmaceutical activities and exists in many natural products [7][8]. The enantioselective synthesis of chiral indolines has received

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• , desulfenylation of VI by anion CF3CO2, afforded 2-thioindole 107 (Scheme 45). The enantioselective synthesis of a broad spectrum of 3-thio-3-pyrrolyloxindoles 109 and 3-seleno-3-pyrrolyloxindoles 110 via sulfenylation and selenenylation of 3-pyrrolyloxindoles 108 was described by Yuan′s research group in 2015

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

Radical ligand transfer: a general strategy for radical functionalization

• David T. Nemoto Jr,
• Kang-Jie Bian,
• Shih-Chieh Kao and
• Julian G. West

Beilstein J. Org. Chem. 2023, 19, 1225–1233, doi:10.3762/bjoc.19.90

• much more efficiently in decarboxylative RLT reactions than aliphatic acids [42]. Outside of decarboxylation, X. Peter Zhang recently reported the enantioselective synthesis of allylic amines through coupled HAT and RLT on allylic C–H bonds [45], using a bulky cobalt porphyrin complex developed and

Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update

• Anup Biswas

Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72

• substitutents. Excellent dia- and enantioselective synthesis of the products were caused by a chiral environment induced in the transition state through a dual H-bonding interaction between both the substrates and catalyst. In addition, π–π stacking between the aromatic moieties in both reagents brought more

Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates

• Bastian Jakob,
• Nico Schneider,
• Luca Gengenbach and
• Georg Manolikakes

Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52

• these transformations to a palladium-catalyzed enantioselective synthesis of α-arylglycine bearing a free carboxylic acid functionality directly from the parent glyoxylic acids (Scheme 1c) [22]. We could show that the desired arylglycine can be synthesized in good to excellent enantioselectivities

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

• Péter Kisszékelyi and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

• . systematically modified atropisomeric C1-symmetric stack ligands to identify suitable catalytic systems for a highly enantioselective synthesis of organoboranes (Scheme 42) [83]. Their best attempt to realize a tandem borylation/aldol cyclization reaction resulted in 72% yield, 90% ee, and a diastereomeric ratio

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

• Jorge de Lima Neto and
• Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

• combretastatin D-1 (1) in 23% overall yield after 16 steps. Later, the same authors performed the enantioselective synthesis of 1 in an attempt to review its absolute configuration [41]. Thus, acetylation of compound 2 followed by the use of Jacobsen’s catalyst [42] to perform the epoxidation of the double bond

• synthesis of combretastatin D-2 (2) by Rychnovsky and Hwang [36]. Divergent synthesis of (±)-1 form combretastatin D-2 (2) by Rychnovsky and Hwang [36]. Enantioselective synthesis of 1 by Rychnovsky and Hwang employing Jacobsen catalyst [41]. Synthesis of fragment 57 by Couladouros and co-workers [43][45

Germacrene B – a central intermediate in sesquiterpene biosynthesis

• Houchao Xu and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

• [112][113][114][115][116], no enantioselective synthesis is available. Full 1H and 13C NMR data of 53 (including 14 carbon signals) have been published [113]. The guaiane sesquiterpenes that are potentially derived from cationic intermediates L1–L4 are summarised in Scheme 16A. trans-β-Guaiene (54) can

Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• chromatography; enantioselective synthesis; GC/MS; semiochemicals; Introduction Hyperolius cinnamomeoventris (Figure 1) is one of the largest species of reed frogs (Hyperoliidae), which are commonly found in Africa, south of the Sahara. Males of the Hyperoliidae possess a characteristic yellow gular patch on

• ) rt, 45 min; e) IBX (3.0 equiv), EtOAc, reflux, 3 h; f) i) CH2=CHMgBr (1.5 equiv) Et2O, 0 °C, ii) rt, 20 min; g) IBX (3.0 equiv), EtOAc, reflux, 6 h; h) i) MeMgBr (1.5 equiv) Et2O, 0 °C, ii) rt, 30 min; j) NaOMe (25.0 equiv), MeOH, rt, 60 h. Enantioselective synthesis with (S)-Jørgensen’s

Synthetic study toward tridachiapyrone B

• Morgan Cormier,
• Florian Hernvann and
• Michaël De Paolis

Beilstein J. Org. Chem. 2022, 18, 1741–1748, doi:10.3762/bjoc.18.183

• chain to the 2,5-cyclohexadienone scaffold. Avoiding heat and light sensitive tetraenes, the convergent plan would also give the opportunity to assess an enantioselective synthesis of the targets, noting that the C14 epimeric product, isotridachiapyrone B, has also been isolated by Schmitz. Results and

Total synthesis of grayanane natural products

• Nicolas Fay,
• Rémi Blieck,
• Cyrille Kouklovsky and
• Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

• to be tackled. A highly enantioselective synthesis is still desirable, as the only synthesis offering >90% ee relies on the combination of chiral ligands and chiral auxiliary. Moreover, to date only 6 natural products from the grayanane family were synthesized, out of the more than 160 compounds

Oxa-Michael-initiated cascade reactions of levoglucosenone

• Julian Klepp,
• Thomas Bousfield,
• Hugh Cummins,
• Sarah V. A.-M. Legendre,
• Jason E. Camp and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2022, 18, 1457–1462, doi:10.3762/bjoc.18.151

• chemistry; levoglucosenone; oxa-Michael reaction; Introduction (−)-Levoglucosenone (1) is formed from the acid-catalyzed pyrolysis of cellulose along with minor amounts of furfural and 5-methylfurfural [1][2][3]. It has emerged as a promising starting material for enantioselective synthesis from materials

Mechanochemical synthesis of unsymmetrical salens for the preparation of Co–salen complexes and their evaluation as catalysts for the synthesis of α-aryloxy alcohols via asymmetric phenolic kinetic resolution of terminal epoxides

• Shengli Zuo,
• Shuxiang Zheng,
• Jianjun Liu and
• Ang Zuo

Beilstein J. Org. Chem. 2022, 18, 1416–1423, doi:10.3762/bjoc.18.147

• enantioselective synthesis in modern chemistry turns out to be accumulatively essential for the preparation of chiral drugs, which is a huge growing market in the future. Indeed, the asymmetric ring opening of terminal epoxides is one of the most important strategies for synthesizing drug-like building blocks and