Oxetanes: formation, reactivity and total syntheses of natural products

• Peter Gabko,
• Martin Kalník and
• Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

Salen–scandium(III) complex-catalyzed asymmetric (3 + 2) annulation of aziridines and aldehydes

• Linqiang Wang and
• Jiaxi Xu

Beilstein J. Org. Chem. 2025, 21, 1087–1094, doi:10.3762/bjoc.21.86

• [5] and the FDA-approved antibiotic linezolid [6] (Figure 1). Both chiral oxazolidines [7][8] and oxazolidinones [9][10] have been utilized as chiral auxiliary groups in many asymmetric organic transformations. Oxazolidine derivatives have been prepared mainly from condensation of vicinal amino

• alcohols and aldehydes [11] and through [2 + 3] cycloaddition of azomethine ylides and carbonyl dipolarophiles [12]. Recently, the [2 + 3] annulation of aldehydes and donor–acceptor dialkyl 2-aryl-1-sulfonylaziridine-2,2-dicarboxylates, which generate azomethine ylides, has been developed for the synthesis

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

• and n-BuLi, followed by a reaction with ZnCl2 at room temperature. The product is then hydrolyzed with a NaOH solution of H2O2 to yield amino alcohols. The mechanism involves the formation of borate intermediate Int-79 from substrate 83 under the action of CH2BrLi. This is followed by an N-1,2

Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt

• Yasushi Yoshida,
• Maho Aono,
• Takashi Mino and
• Masami Sakamoto

Beilstein J. Org. Chem. 2025, 21, 547–555, doi:10.3762/bjoc.21.43

• , Chiba 263-8522, Japan 10.3762/bjoc.21.43 Abstract β-Amino cyanoesters are important scaffolds because they can be transformed into useful chiral amines, amino acids, and amino alcohols. Halogen bonding, which can be formed between halogen atoms and electron-rich chemical species, is attractive because

• excellent enantioselectivities (Figure 1c). Despite these successful examples, the construction of only one stereocenter has been reported to date. The Mannich reaction has great importance because of its utility in the preparation of useful chiral molecules such as amines [36], amino acids [37], and amino

• alcohols [38]. In this context, their asymmetric syntheses are important and have also been researched mainly using chiral catalysts [39][40]. Previously, the Mannich reaction has been applied in the construction of contiguous stereogenic centers (Figure 2). In 2005, Jørgensen and co-workers reported the

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA

• Laurin Flemmich and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

• . First, the alkyl handles bearing a primary hydroxy group were introduced and then converted into the electrophile of choice. More specifically, to furnish compounds 4b–d, precursor 9 was treated with the corresponding amino alcohols in the presence of a desiccant. The imines formed were subjected to

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

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

• Mohd Farhan Ansari,
• Atul Kumar Maurya,
• Abhishek Kumar and
• Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

• ]. A variety of amino alcohols and alcohols were investigated with Mn4 (0.5 mol %) and t-BuOK (1.5 equiv) in 2-MeTHF under reflux conditions and the corresponding pyrroles were isolated with up to 93% yield (Scheme 69). Notably, the same pincer ligand-supported Co and Fe complexes showed no activity in

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

• products 4a and 6a (Scheme 6). Both model reactions with diene 2a and allene 5a were proven to be easily scalable without further conditions optimization, delivering unsaturated γ- and ε-AA derivatives 4a and 6a in good yields. Starting from the unsaturated ε-AA derivative 4a, unsaturated ζ-amino alcohols

Complexes of resorcin[4]arene with secondary amines: synthesis, solvent influence on “in-out” structure, and theoretical calculations of non-covalent interactions

• Waldemar Iwanek

Beilstein J. Org. Chem. 2023, 19, 1525–1536, doi:10.3762/bjoc.19.109

• ], amino alcohols [10], and amino acids [11] have been studied due to their potential applications in supramolecular chemistry, drug delivery, and molecular recognition. The complexation of R[4]A with amines is based on the formation of hydrogen bonds between the hydroxy groups of the resorcinol units and

α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping

• Angel Palillero-Cisneros,
• Paola G. Gordillo-Guerra,
• Fernando García-Alvarez,
• Olivier Jackowski,
• Franck Ferreira,
• Fabrice Chemla,
• Joel L. Terán and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103

• stereocenter. α-(Aminomethyl)acrylates 5–7 reacted smoothly at −33 °C within 2 h with Et2Zn in the presence of cyclohexanone to afford amino alcohols 18–20 in quite good yields (63–68%). Even better yields were obtained with enoates 8a and 8b both with cyclohexanone and acetone as carbonyl partners. Starting

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

• Emine Salamci and
• Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

• antibiotic activities. Therefore, synthetic methodologies for the preparation of the aziridinyl system have attracted attention in recent decades. Opening of the aziridine ring by using different nucleophiles gives the corresponding amino alcohols, amino esters, azido amines, amines, and other derivatives [9

Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

• Md Imran Hossain,
• Md Imdadul H. Khan,
• Seong Jong Kim and
• Hoang V. Le

Beilstein J. Org. Chem. 2022, 18, 446–458, doi:10.3762/bjoc.18.47

• and γ-amino alcohols [1]. Isoxazoles, appearing in 33 patents from the year 2016 to 2018 [3], are an important drug class due to their wide range of biological activities, such as anticancer [5], antibiotic [6][7], antimicrobial [8], antifungal [9], and anti-inflammatory [10]. Therefore, new methods

Cs₂CO₃-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones

• Ol'ga G. Volostnykh,
• Olesya A. Shemyakina,
• Anton V. Stepanov and
• Igor' A. Ushakov

Beilstein J. Org. Chem. 2022, 18, 420–428, doi:10.3762/bjoc.18.44

• building blocks for the production of other important molecules (e.g., amino alcohols, diols, etc.) [40][41][42][43][44][45][46] and potential pharmaceuticals. α-Hydroxyketones are structural subunits of natural products [47][48][49] and compounds possessing immunosuppressant [50], antidepressant [51

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines

• Yelong Lei and
• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 70–76, doi:10.3762/bjoc.18.6

• synthesis of oxazoline derivatives [11][12]. They mainly include (1) cyclization of 2-amidoethyl halides or sulfonates, which are prepared from carboxylic acid derivatives and vicinal amino alcohols [8][9][10] (Scheme 1a); (2) direct condensation of carboxylic acid derivatives or nitriles with vicinal amino

• alcohols [13][14][15] (Scheme 1a); (3) oxidative condensation of aldehydes with vicinal amino alcohols [16] (Scheme 1b); (4) cyclization of N-allylamides in the presence of electrophilic reagents or radical initiators or catalysts [17] (Scheme 1c); (5) direct synthesis from alkenes and amides or nitriles

Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

• Alemayehu Gashaw Woldegiorgis and
• Xufeng Lin

Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185

• materials and supramolecules. Important chiral phosphoric acid scaffolds used in this review. Atroposelective aryl–aryl-bond formation by employing a facile [3,3]-sigmatropic rearrangement. Atroposelective synthesis of axially chiral biaryl amino alcohols 5. The enantioselective reaction of quinone and 2

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

Recent developments in enantioselective photocatalysis

• Callum Prentice,
• James Morrisson,
• Andrew D. Smith and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis

• David Van Craen,
• Jenny Begall,
• Johannes Großkurth,
• Leonard Himmel,
• Oliver Linnenberg,
• Elisabeth Isaak and
• Markus Albrecht

Beilstein J. Org. Chem. 2020, 16, 2338–2345, doi:10.3762/bjoc.16.195

• the amino alcohols 10a–d were protected with a Boc group [42][43]. Esterification of the protected alcohols 11a–d [33][44] with 2,3-dioxosulfinylbenzoyl chloride obtained from 2,3-dihydroxybenzoic acid and thionyl chloride afforded the N-Boc-substituted catechol ligands 12a–d [33][36]. They were

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• oxazolidinones and five-membered cyclic carbonates of various structures. The most well-known strategies for the synthesis of oxazolidinones are the reaction of an amino alcohol with phosgene [5][22], the carbonylation reaction of β-amino alcohols with CO2 or dialkyl carbonates [23][24][25][26][27], the

• shorter reaction times under mild conditions using a simple purification method. Apparently, our protocol describes a reasonable methodology for the conversion of epoxides to protected 1,2-diols and 2-amino alcohols. Attention is drawn on these 1,2-oxygen and/or nitrogen units since they are present in

• using a safe, inexpensive, metal-free reagent, a simple purification method and shorter reaction times via a one-pot reaction. The study presents a useful method for one-pot conversion of epoxides to protected 1,2-diols and 2-amino alcohols in one reaction. In the computational part of the study, the

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

• Marcin Kaźmierczak and
• Henryk Koroniak

Beilstein J. Org. Chem. 2020, 16, 756–762, doi:10.3762/bjoc.16.69

• shown that the regioselectivity of the nucleophilic fluorination of amino alcohols can be controlled depending on the fluorinating reagent used [30][31]. This work presents the optimization of nucleophilic fluorination conditions. What is more, we discuss the effect of the base used on the

• Pudovik reaction, but also improved its yield drastically (Table 1). The implementation of this allowed us to obtain the anti-isomer (1R,2S) in very good yields. There are not many literature examples of the regioselective fluorination of amino alcohols using by PyFluor (1) or PBSF (2). In general, the

• atmosphere while the reaction medium was toluene. In the first stage of the optimization three representative amino alcohols were chosen. Each bearing a different group in the side chain: an aromatic (5a), a small (5b) and a large aliphatic substituent (5c). Unfortunately, under the tested conditions, we did

Recent advances in Cu-catalyzed C(sp³)–Si and C(sp³)–B bond formation

• Balaram S. Takale,
• Ruchita R. Thakore,
• Elham Etemadi-Davan and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

• silyl ethers 89–92 (Scheme 18), thus showcasing the synergistic relationship between Pd and Cu catalysis [43]. Driven by the success of earlier results, the authors utilized 78 for reductive couplings between ketones 93 and imines 97 as electrophiles to form unsymmetrical 1,2-diols 94–96 and 1,2-amino

• alcohols 98–100, respectively. Palladium was no longer needed for these transformations. The scope of the reaction with ketones was not limited to diaryl species and aryl ketones participated in the reaction, including those with more hindered alkyl groups (Scheme 19) [44]. This discovery was followed by a

KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones

• Qiao Lin,
• Shiling Zhang and
• Bin Li

Beilstein J. Org. Chem. 2020, 16, 492–501, doi:10.3762/bjoc.16.44

• coordination chemistry, and also valuable protecting or directing groups in catalysis [1][2][3]. 2-Oxazolines are a readily stable class of heterocycles resistant to a range of nucleophiles, bases, or radicals [4][5], which can be easily generated from amino alcohols and carboxylic acids, and from alkenes or