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

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• for most POx, accordingly, it was used successfully only for the polymerization of EtOx [34]. Correia et al. used supercritical carbon dioxide for the synthesis of 2-oxazoline-based oligomers with antimicrobial properties and applied boron trifluoride etherate as the initiator [35]. However, carbamic

• Dihydrolevoglucosenone (DLG) is prepared by hydrogenation of levoglucosenone in the presence of palladium as a catalyst. Recently, Debsharma et al. reported the CROP of levoglucosenyl alkyl ether in CH2Cl2 at 0 °C and at room temperature using triflic acid or boron trifluoride etherate as initiators [46][47][48]. The 1H

Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation

• Lukáš Ďurina,
• Anna Ďurinová,
• František Trejtnar,
• Ľuboš Janotka,
• Lucia Messingerová,
• Jana Doháňošová,
• Ján Moncol and
• Róbert Fischer

Beilstein J. Org. Chem. 2021, 17, 2781–2786, doi:10.3762/bjoc.17.188

• terminal alkenes bearing both an allylic and homoallylic-type hydroxy group, yielding a sole threo isomer, are rare [36]. The cyclization of 5 through an epoxide ring-opening reaction with boron trifluoride etherate in dichloromethane at 0 °C yielded pyrrolidine derivative 12 in 69% isolated yield [37

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

• by Humber et al. [45]. They started with a coupling reaction of (+)-thiolactic acid 3p and 2-benzoyloxyacetaldehyde (3a) using boron trifluoride etherate. A diastereomeric mixture of oxathiolane acids 29 and 30 was prepared in a 1:2 ratio in good yield (Scheme 7). Further separation of the

Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction

• Dušan Đ. Škorić,
• Olivera R. Klisurić,
• Dimitar S. Jakimov,
• Marija N. Sakač and
• János J. Csanádi

Beilstein J. Org. Chem. 2021, 17, 2611–2620, doi:10.3762/bjoc.17.174

• noticeably, while the yield was preserved. Ketone 3 and enone 4 were used for the optimization of reaction conditions. Firstly, the ketone 3 was reacted with hydrazoic acid in the presence of boron trifluoride etherate as a Lewis acid (Table 1, entry 1). The desired tetrazole 13 was obtained after

• trifluoride etherate (1.15 mL) were placed. The mixture was cooled with an ice water bath, and a benzene solution of the carbonyl compound (1.50 mmol in 15 mL of benzene) was added dropwise over 40 minutes with stirring and cooling. After the addition was completed, the reaction mixture was left at room

• for the preparation of tetrazoles with hydrazoic acid Caution: Hydrazoic acid should be handled with care in an efficient fume hood since it is toxic and explosive. In a two-neck round-bottom flask equipped with an addition funnel and argon inlet, a benzene solution of hydrazoic acid (18 mL) and boron

Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones

• Robin Klintworth,
• Garreth L. Morgans,
• Stefania M. Scalzullo,
• Charles B. de Koning,
• Willem A. L. van Otterlo and
• Joseph P. Michael

Beilstein J. Org. Chem. 2021, 17, 2543–2552, doi:10.3762/bjoc.17.170

• , methanesulfonic acid, boron trifluoride etherate) resulted in decomposition if the reactions were left at room temperature overnight, or within ten minutes if the temperature was raised, even to 50 °C (Table 1, entries 6–13). The enaminone appeared to be protonated at room temperature, presumably on the oxygen

Facile and innovative catalytic protocol for intramolecular Friedel–Crafts cyclization of Morita–Baylis–Hillman adducts: Synergistic combination of chiral (salen)chromium(III)/BF₃·OEt₂ catalysis

• Karthikeyan Soundararajan,
• Helen Ratna Monica Jeyarajan,
• Raju Subimol Kamarajapurathu and
• Karthik Krishna Kumar Ayyanoth

Beilstein J. Org. Chem. 2021, 17, 2186–2193, doi:10.3762/bjoc.17.140

• -substituted-1H-indenes from unique substrates of Morita–Baylis–Hillman adducts via an easy operating practical procedure. Keywords: boron trifluoride etherate; chiral (salen)chromium(III); intramolecular Friedel–Crafts cyclization; Morita–Baylis–Hillman adducts; substituted-1H-indenes; Introduction

• in MBH adduct 5a (Table 1, entries 14–17). Interestingly among all co-catalysts examined, boron trifluoride etherate was the found to be the suitable co-catalyst in accelerating the proposed reaction. Furthermore on screening the optimized catalytic combination in presence of alternative solvents

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

• 90% yield. A Lewis acid-promoted cyclization (boron trifluoride etherate at 60 °C) avoided the use of high temperatures, while providing the products in comfortable yields. Dicyanamide has also been shown to react with hydroxylamine hydrochloride to form [1,2,4]oxadiazole-3,5-diamine (Scheme 29A) [49

The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization

• Sharna-kay Daley and
• Nadale Downer-Riley

Beilstein J. Org. Chem. 2020, 16, 2026–2031, doi:10.3762/bjoc.16.169

• FeCl3·SiO2. Treatment of the polyphenol with PIDA (1.5 equiv) in boron trifluoride etherate (1.5 mL) at room temperature proved to be the most successful dimerization protocol, as the dimeric precursor 19 was formed in 80% yield after 16 hours. The biaryl 19 was converted quantitatively to the natural

Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions

• Clément Q. Fontenelle,
• Thibault Thierry,
• Romain Laporte,
• Emmanuel Pfund and
• Thierry Lequeux

Beilstein J. Org. Chem. 2020, 16, 1936–1946, doi:10.3762/bjoc.16.160

• can be stopped at the alcohol stage when performed in the presence of BF3·Et2O instead of CSA to afford alkene Z-13 as the major product. The use of boron trifluoride etherate as an activator combined with TBAB afforded exclusively alkene Z-13 as evidenced by TLC, but after work-up, 22% of the

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

Synthesis of the aglycon of scorzodihydrostilbenes B and D

• Katja Weimann and
• Manfred Braun

Beilstein J. Org. Chem. 2019, 15, 610–616, doi:10.3762/bjoc.15.56

• -D-glucose pentaacetate in the presence of an excess of boron trifluoride etherate [20], a regioselective reaction occurred at the phenolic group in ortho-position to the alkyl side chain to give mono-glycosylated product 12. Chelation of the carbonyl and the neighboring phenolic group by the Lewis

• trifluoride etherate (0.4 mL, 3.12 mmol) were injected by syringe. The mixture was stirred at 25 °C for 2 d. Thereafter, saturated aqueous sodium hydrogen carbonate (10 mL) was added and the mixture was extracted five times with 15 mL portions of dichloromethane. The combined organic layers were washed with

• equipped with a stirring bar and a connection to the combined nitrogen/vacuum line. The flask was charged with dihydrostilbene 9 (330 mg, 1.04 mmol) and β-glucose pentaacetate (814 mg, 2.08 mmol) and closed with a septum. The air in the flask was replaced by nitrogen. Then, dichloromethane (4 mL) and boron

Synthesis of nonracemic hydroxyglutamic acids

• Dorota G. Piotrowska,
• Iwona E. Głowacka,
• Andrzej E. Wróblewski and
• Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

• cleanly liberates (2S,3S,4S)-4 (Scheme 25) [100]. This methodology opens the way to (3S,4S)-3-hydroxy-4-methoxy- (104) and 3,4-dimethoxy-L-glutamic acid (105) since selective opening of the lactone ring in 95 can be accomplished by boron trifluoride etherate-catalyzed methanolysis at low temperatures to

• trifluoride etherate-catalyzed reaction of 95 with benzyl alcohol induces first opening of the 5-membered ring to form a benzyl ester and later the cleavage of the 3-membered ring to give a vicinal N-Cbz aminoalcohol with inversion of configuration. However, the reaction mixture (1:1) consists of the

• decomposition of this stereoisomer including racemization at Cα. From pentose via 2,3-aziridino-γ-lactone In the so called “2,3-aziridino-γ-lactone methodology” [18][99][100] ribose (or lyxose) is used as a starting material [101][102] which is transformed into the lactone 95 in several steps [99]. Boron

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

• depicted in Scheme 38 (Scheme 45) [161]. Sato’s group reported the synthesis of 7-hydroxy-2,3-benzotropone (241) via the ring expansion pathway of β-naphthoquinone (280) with diazomethane under various conditions and hydrolysis steps (Scheme 46) [169]. The boron trifluoride etherate-promoted ring expansion

cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

• Dimpee Gogoi,
• Runjun Devi,
• Pallab Pahari,
• Bipul Sarma and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2016, 12, 2816–2822, doi:10.3762/bjoc.12.280

• under metal-free conditions and the operational simplicity render this transformation an attractive approach. Nevertheless, in an additional work, the angular –OH group of (±)-5k was reductively removed on treatment with Et3SiH and boron trifluoride etherate to get chroman-fused tetralin (±)-14 with the

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

• peroxide 115, which rearranges through an acid-catalyzed Baeyer–Villiger-type rearrangement into 116. Hydroxy-10H-acridin-9-ones 117 proved to be promising antipsoriatic agents [287]. The oxidation of aldimines 118a–f with m-chloroperbenzoic acid in the presence of boron trifluoride etherate produces

Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction

• Madhuri V. Shinde,
• Rohini S. Ople,
• Ekta Sangtani,
• Rajesh Gonnade and
• D. Srinivasa Reddy

Beilstein J. Org. Chem. 2015, 11, 1060–1067, doi:10.3762/bjoc.11.119

• ·OEt2 Boron trifluoride etherate (0.07 mL, 0.71 mmol) was added to a solution of azido alcohol 3 (0.10 g, 0.71 mmol) and ketones (2.0 mmol, 3 equiv) in HFIP (0.2 mL) cooled to 0 °C. The mixture was warmed to room temperature and stirred for 2–5 h. Upon completion, the reaction was quenched with 15% aq

Redox active dendronized polystyrenes equipped with peripheral triarylamines

• Toshiki Nokami,
• Naoki Musya,
• Tatsuya Morofuji,
• Keiji Takeda,
• Masahiro Takumi,
• Akihiro Shimizu and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2014, 10, 3097–3103, doi:10.3762/bjoc.10.326

•  2. Di(p-bromophenyl)carbinol (1) was treated with SOCl2 to obtain di(p-bromophenyl)methyl chloride (2) in quantitative yield. A Friedel–Crafts-type alkylation [29] of diphenylsilane 3 with 2 in the presence of boron trifluoride etherate as a Lewis acid gave 4 in 86% yield. The oxidation potential of

An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y

• Suresh Babu Meruva,
• Akula Raghunadh,
• Raghavendra Rao Kamaraju,
• U. K. Syam Kumar and
• P. K. Dubey

Beilstein J. Org. Chem. 2014, 10, 471–480, doi:10.3762/bjoc.10.45

• ). General procedure for the synthesis of dihydroeudistomin (7a–7j) To a stirred solution of N-(2-(1H-indol-3-yl)ethyl)-2-oxo-2-phenylacetamide (9a, 2.0 g, 6.8 mmol) in diethyl ether (20 mL) was added 48% boron trifluoride etherate (10.1 g, 34.2 mmol) in a round-bottom flask under a N2 atmosphere, and the

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

• Alexander O. Terent'ev,
• Dmitry A. Borisov,
• Vera A. Vil’ and
• Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• diastereoisomers. The Lewis acid induced key step, a domino epoxide-opening/rearrangement/cyclization cascade, most likely proceeded in a stepwise manner via intermediate 179. Activation of the epoxide with boron trifluoride etherate induces the planned sigmatropic [1,2]-methyl and [1,2]-hydride shifts to generate

• prenyl side chain and introduction of the formyl group was accomplished within five steps to give 191a (Scheme 25). The envisioned deprotection of 191a using Lewis acidic conditions led to an unexpected and unprecedented metal-free carbonyl–olefin metathesis. Coordination of boron trifluoride etherate to

Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

• Elizabeth P. Jones,
• Peter Jones,
• Andrew J. P. White and
• Anthony G. M. Barrett

Beilstein J. Org. Chem. 2011, 7, 1570–1576, doi:10.3762/bjoc.7.185

• electrophile in the presence of boron trifluoride etherate (Table 1, entry 10) gave alcohol 6j. When (S)-propylene oxide was used instead there was no reaction, and indeed Schöllkopf noted significant levels of kinetic resolution when such reactions were performed with racemic oxiranes [23]. In our previous

CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF₃ and BH₃

• Julien Monot,
• Louis Fensterbank,
• Max Malacria,
• Emmanuel Lacôte,
• Steven J. Geib and
• Dennis P. Curran

Beilstein J. Org. Chem. 2010, 6, 709–712, doi:10.3762/bjoc.6.82

• dichloride salt 1a with NaHMDS in THF at −78 °C, followed by warming to room temperature gave a pale yellow solution of the free carbene 2a [20]. A broad resonance at −312 ppm in the 13C NMR spectrum of this solution indicated that 2a had formed. Boron trifluoride etherate (BF3•Et2O) was then added at −78 °C

New amphiphilic glycopolymers by click functionalization of random copolymers – application to the colloidal stabilisation of polymer nanoparticles and their interaction with concanavalin A lectin

• Otman Otman,
• Paul Boullanger,
• Eric Drockenmuller and
• Thierry Hamaide

Beilstein J. Org. Chem. 2010, 6, No. 58, doi:10.3762/bjoc.6.58

• best result was obtained with commercially available triethylene glycol monochloride. Thus, peracetylated mannose 1 was reacted with triethyleneglycol monochloride, in the presence of boron trifluoride etherate to afford glycoside 2 [12] in 50–55% yield. After purification, the latter was converted to

Acid catalyzed cyclodimerization of 2,2-bis(trifluoromethyl)-4-alkoxy-oxetanes and -thietanes. Synthesis of 2,2,6,6-tetrakis(trifluoromethyl)-4,8-dialkoxy-1,5-dioxocanes and 3,3,7,7-tetrakis(trifluoromethyl)-9-oxa-2,6-dithia-bicyclo[3.3.1]nonane

• Viacheslav A. Petrov and
• Will Marshall

Beilstein J. Org. Chem. 2010, 6, No. 46, doi:10.3762/bjoc.6.46

• different reaction course. The addition of boron trifluoride etherate catalyst to a solution of the oxetane in dichloromethane resulted in a spontaneous and mildly exothermic reaction. A very interesting feature of this process is the appearance of highly intensive blue or blue-green colour upon the