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

• -acylimidazoles with potassium alkenyl trifluoroborates under mild electrochemical conditions (Scheme 41). This method provides an efficient and enantioselective approach to C(sp3)–H alkenylation, demonstrating the potential of combining chiral catalysis with electrochemistry for the functionalization of complex

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

• Prodip Howlader and
• Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

• catalysts has been successfully developed employing dynamic metal–ligand coordination bonds. While only a small fraction of these 3D architectures was useful for chiral catalysis, an even smaller fraction was able to provide a high stereoselectivity during asymmetric catalysis [5]. For instance, an

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• ][22][23]. On the other hands, further extension of these molecules leads to homochiral carbon nanotubes which can produce innovative perception in chiral sensing, chiral catalysis, separation techniques and chiral ligands for organocatalysis [24]. Additionally, control on the bowl-to-bowl inversion

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

• efficiency of a 2-substituted N-(1-phenylethyl)aziridine framework as chiron bearing a chiral auxiliary. Keywords: alkaloids; amino acids; asymmetric synthesis; ceramides; chiral catalysis; chiral pool; N-(1-phenylethyl)aziridine chiron; sphingoids; Introduction The synthesis of enantiomerically pure

Enantioselective Diels–Alder reaction of anthracene by chiral tritylium catalysis

• Qichao Zhang,
• Jian Lv and
• Sanzhong Luo

Beilstein J. Org. Chem. 2019, 15, 1304–1312, doi:10.3762/bjoc.15.129

• synthesize stabilized chiral carbocations with chirality installed onto their backbones. Pioneering efforts along this line by Kagan, Sammakia, and Chen have shown that chiral catalysis with such chiral carbocations was indeed plausible to achieve stereocontrol (Scheme 1a). [14][15][16][17][18][19]. However

• -developed and we next examined the scope with substituted anthracenes. Unfortunately, these well-explored substrates did not work in our chiral catalysis system giving either no activity or poor enantioselectivity, particularly in cases of 9-monosubstituted anthracenes. When 9,10-dimethylanthracene (3b) was

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

• pyroglutamic acids, proline and 4-hydroxyproline). Since various hydroxyglutamic acids were identified as components of complex natural products, syntheses of orthogonally protected derivatives of hydroxyglutamic acids are also covered. Keywords: amino acids; asymmetric synthesis; chiral catalysis; chiral

Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

• M. Fernanda N. N. Carvalho,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2017, 13, 1230–1238, doi:10.3762/bjoc.13.122

• ][11]. From cheap camphor-10-sulfonic acid (1), a cyclic sulfonimide 2 can easily be obtained which is readily converted into useful auxiliaries [12], or oxidized to the oxoimide 3 (Scheme 1) [13][14][15]. This versatile intermediate can be reduced to provide a chelating ligand for chiral catalysis [16

Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis

• Flavio Fanelli,
• Giovanna Parisi,
• Leonardo Degennaro and
• Renzo Luisi

Beilstein J. Org. Chem. 2017, 13, 520–542, doi:10.3762/bjoc.13.51

• produce enantioenriched materials were employed. It is worth mentioning that this work represents a very nice example on the use of chiral catalysis in a multistep flow synthesis of a drug target on gram scale. The multistep synthesis of (S)-rolipram reported in Scheme 23 begins from a benzaldehyde

Enantioselective carbenoid insertion into C(sp³)–H bonds

• J. V. Santiago and
• A. H. L. Machado

Beilstein J. Org. Chem. 2016, 12, 882–902, doi:10.3762/bjoc.12.87

• activation; chiral catalysis; diazo compounds; total synthesis; Introduction One of the major challenges met in organic synthesis is the formation of carbon–carbon bonds, in particular in a stereoselective way. Nucleophilic substitution reactions, radical reactions, cross-coupling reactions and the Heck

Self and directed assembly: people and molecules

• Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

• ) who as it happens had employed Susumu Arimori after he left my group at the end of 2001 as a Post-Doctoral Research Fellow. The two weeks on the road also allowed Steve and me to discuss research. Steve is interested in chiral catalysis and I am interested in chiral sensing so a collaborative project

Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination

• Łukasz Górecki,
• Artur Mucha and
• Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 883–889, doi:10.3762/bjoc.10.85

• : aromatic quinoline and chiral aliphatic quinuclidine, and a hydroxy function on the stereogenic carbon atom. Such an architecture combined with the presence of nucleophilic and electrophilic centers buried in a hydrophobic environment predestinates the molecule to asymmetric applications, such as: chiral

• catalysis, transition metal complexing, molecular recognition, chromatographic separation and analysis of enantiomers [2][3][4][5]. Synthetic modifications of the basic structure, motivated by an improved stereoselectivity potential of quinine, are an issue of ongoing trials [6][7][8][9]. Surprisingly

Approaches to α-amino acids via rearrangement to electron-deficient nitrogen: Beckmann and Hofmann rearrangements of appropriate carboxyl-protected substrates

• Sosale Chandrasekhar and
• V. Mohana Rao

Beilstein J. Org. Chem. 2012, 8, 1393–1399, doi:10.3762/bjoc.8.161

• be investigated (most notably the Strecker reaction) [2], but recent developments focus on cycloadditions [3], rare amino acids [4], chiral catalysis [5], etc. It is noteworthy, however, that two of the most widely applied methods for the introduction of the amine group – the Beckmann [6][7][8][9

Enantiospecific synthesis of [2.2]paracyclophane- 4-thiol and derivatives

• Gareth J. Rowlands and
• Richard J. Seacome

Beilstein J. Org. Chem. 2009, 5, No. 9, doi:10.3762/bjoc.5.9

• enantiomerically pure derivatives have been utilised in chiral catalysis [10][11] and as probes for biological recognition processes [12][13][14], the full potential of these systems has not been realised due to the difficulties encountered when trying to access enantiomerically pure [2.2]paracyclophane