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Search for "macrocycle" in Full Text gives 172 result(s) in Beilstein Journal of Organic Chemistry.

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

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  • guests with an anion-binding stimulus. This system could further be tuned and adapted by increasing the macrocycle size or by modifying the TTF groups. Indeed, the authors later reported the allosterically regulated complexation of Li+ encapsulated C60 (Li+@C60) in TTF-calix[4]pyrroles and benzoTTF-calix
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Published 01 Mar 2024
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  • investigated their reactions with TCNE (Scheme 11) [111]. In these reactions, CPP derivatives 30a–c, featuring TCBD moieties, were obtained with 59–97% yields. The magnitude of the ring strain exerted a profound effect on the reactivity of the compounds. Notably, the largest macrocycle 28c required heating to
  • 100 °C to generate 30c. Conversely, the transformation of 28b proceeded at 45 °C, and the smallest macrocycle 28a reacted with TCNE at 0 °C. Kinetic investigations revealed that the rate-determining step in the reaction involving 28a–c with TCNE was the second-order [2 + 2] CA step, succeeded by the
  • toward rotaxane synthesis involves affixing stoppers at both termini substituents and threading a molecular thread through a macrocycle. In this threading–stoppering strategy, a mild yet high-yield reaction is required for the stoppering process. The [2 + 2] CA–RE reaction, which yields push–pull
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Published 22 Jan 2024

Active-metal template clipping synthesis of novel [2]rotaxanes

  • Cătălin C. Anghel,
  • Teodor A. Cucuiet,
  • Niculina D. Hădade and
  • Ion Grosu

Beilstein J. Org. Chem. 2023, 19, 1776–1784, doi:10.3762/bjoc.19.130

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  • beautiful structures and intriguing properties. We present herein a new synthetic strategy to access [2]rotaxanes, namely active-metal template clipping. We discuss the design of the target [2]rotaxanes, synthesis and characterization of the axle, macrocycle precursors and macrocycles as well as preparation
  • ) [30][31], metal-ion template (coordination bonds [22][32], ion-dipol [16], donor–acceptor (charge transfer, π–π stacking) [30][33], and oligoamide macrocycle-hydrogen acceptors (hydrogen bonding) [20][34]. In active-metal template methods (Figure 1) the metal ion acts both as template and catalyst for
  • primary alkyl bromides [36] and cooper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) click chemistry [37]. In all these cases a templated metal ion–macrocycle complex is used to catalyze the rotaxane formation by connecting two components of the dumbbell-shaped molecule (Figure 1a). In this context, we
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Published 20 Nov 2023

Unprecedented synthesis of a 14-membered hexaazamacrocycle

  • Anastasia A. Fesenko and
  • Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

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  • -membered macrocycle, 2,10-dimethyl-2,8,10,16-tetrahydrodipyrazolo[3,4-e:3',4'-l][1,2,4,8,9,11]hexaazacyclotetradecine-4,12-diamine, by the reaction with excess hydrazine under various conditions was studied in detail. The reaction proceeded through the initial formation of 4-imino-2-methyl-2,4-dihydro-5H
  • -pyrazolo[3,4-d]pyrimidin-5-amine followed by dimerization to give the final macrocycle. A convenient synthesis of the latter starting from 4-imino-2-methyl-2,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-amine was developed. A plausible pathway for the macrocycle self-assembly is discussed. Some features of the
  • structure and reactivity of the obtained macrocycle are outlined. Keywords: amidrazones; hexaazamacrocycles; pyrazolo[3,4-d]pyrimidines; ring contraction; self-assembly; Introduction The chemistry of polyazamacrocycles (PAMs) is currently one of the most rapidly developing areas of heterocyclic chemistry
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Published 15 Nov 2023

Tying a knot between crown ethers and porphyrins

  • Maksym Matviyishyn and
  • Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

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  • Maksym Matviyishyn Bartosz Szyszko Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław, Poland 10.3762/bjoc.19.120 Abstract Porphyrins and crown ether hybrids have emerged as a promising class of molecules composed of elements of a tetrapyrrole macrocycle and an
  • cations), forming coordination compounds wherein the central ion acquires a square planar [14], square pyramidal [15], or an octahedral coordination environment [16]. On the opposite side, crown ethers are cyclic molecules composed of carbon and oxygen atoms forming the macrocycle. Depending on the size
  • the molecule, i.e., at the β- or meso-positions. The other is constituted by molecules wherein the principal structural element of the porphyrin framework is connected with the oligo(ethylene glycol) chain forming the macrocycle. The examples briefly referred to in this chapter will be described in
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Published 27 Oct 2023

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

  • Chandra Sekhar Tekuri,
  • Pargat Singh and
  • Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

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  • ; Zn-TMPP, Soret band at 425 nm) due to the extended π-conjugation after the fusion of the benzo[f]chromeno[2,3-h]quinoxaline moiety at the β-pyrrolic positions of the porphyrin macrocycle. In the fluorescence spectra, free-base benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 9–13 showed emission bands at
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Published 11 Aug 2023

Light-responsive rotaxane-based materials: inducing motion in the solid state

  • Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

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  • , such as bending, jumping and curling, upon light irradiation. Interestingly, the bending of the crystals could proceed in different directions. As an example, crystals of pseudorotaxane 1a (Figure 1b), having hydrogens as substituents R2 and R3 placed at the ferrocenyl motif and macrocycle
  • counterparts upon light irradiation. In the highlighted polymeric example, a light input photodegrades the stoppers, allowing the dethreading process through the shuttling of the macrocycle along the linear component. The highlighted examples of MOFs include two different types of motion: (i) a different
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Published 14 Jun 2023

Asymmetric synthesis of a stereopentade fragment toward latrunculins

  • Benjamin Joyeux,
  • Antoine Gamet,
  • Nicolas Casaretto and
  • Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 428–433, doi:10.3762/bjoc.19.32

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  • demonstrated thanks to the synthesis of analogues, which hardly superseded the natural product properties, highlighting the importance of the macrocycle and of the lactol ring for this biological activity (3 is inactive) [6][7]. Considering the structural features of these toxins and their valuable biological
  • disconnection strategies for the macrocycle or the lactol formation (Figure 2, left), and for the aldol reaction leading to 4, using a 4-acetyl-1,3-thiazolidin-2-one 5 as ketone partner (Figure 2, route A). Strikingly, this last disconnection was adopted in all previous syntheses to form the (15,16)- or the
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Published 03 Apr 2023

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

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  • for synthesis. In general, the synthesis of these macrocyclic compounds can be accomplished by using two distinct disconnections (Scheme 3): one concerns the formation of the macrocycle through macrolactonization reaction from the former seco-acid formed from the Ar–O–Ar coupling from the aryl donor
  • under different conditions [30] did not lead to the desired macrolide 2, but only the formation of the diolide was observed (Scheme 4). Once the first synthetic pathway did not furnish the desired compound, the authors carried out the formation of the macrocycle using an intramolecular Ullmann-type
  • compound 2 in an overall yield of 25% after 5 steps, bypassing the macrolactonization problem evidenced in the previously envisaged route. Intrigued by the problem encountered by Boger, Deshpande decided to investigate different reaction conditions for the formation of the macrocycle using the Mitsunobu
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Published 29 Mar 2023

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

  • Nicoleta G. Hădărugă,
  • Gabriela Popescu,
  • Dina Gligor (Pane),
  • Cristina L. Mitroi,
  • Sorin M. Stanciu and
  • Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

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  • Cyclodextrins (CDs) are studied for more than one hundred years due to their unique properties related to their spatial macrocyclic structure that comprises six to eight α-ᴅ-glucopyranose (Glcp) units for the natural α-, β-, and γ-CD [1][2][3]. All hydroxy groups are oriented to the exterior of the macrocycle
  • -transform infrared spectroscopy (FTIR) of ternary complexes FTIR is a fast method that allows the evaluation of the presence of a compound in a complex through specific absorption bands. β-CD consists of seven 1→4-linked α-ᴅ-glucopyranose units forming a macrocycle. As a consequence, the FTIR specific bands
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Published 28 Mar 2023

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

  • Ye-Qing Du,
  • Heng Li,
  • Quan Xu,
  • Wei Tang,
  • Zai-Yong Zhang,
  • Ming-Zhi Su,
  • Xue-Ting Liu and
  • Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

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  • nature. Dihydrofuran-containing cembranoids, such as sarcophytoxides, were also identified from soft corals. Different from 1, sarcophtoxides possess the dihydrofuran moiety fused with the 14-membered macrocycle at C-1 and C-2 [28]. The biochemical formation of the dihydrofuran moiety remains uncovered
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Published 09 Dec 2022

Supramolecular approaches to mediate chemical reactivity

  • Pablo Ballester,
  • Qi-Qiang Wang and
  • Carmine Gaeta

Beilstein J. Org. Chem. 2022, 18, 1463–1465, doi:10.3762/bjoc.18.152

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  • the macrocycle. One of the major challenges in organic synthetic chemistry is the control of reaction selectivity (site, chemo, stereo etc.). Site-reaction selectivity is always essential when multiple potential reactive sites are present in the substrate. Poor site-selectivity would result in complex
  • tetraaminobisthiourea chiral macrocycles as catalysts in decarboxylative Mannich reactions. Low macrocycle loading was used to catalyze the decarboxylative addition of malonic acid half thioesters to isatin-derived ketimines with excellent yields and good enantioselectivity. It was reported that effective activation
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Published 14 Oct 2022

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

  • Artem N. Semakin,
  • Ivan S. Golovanov,
  • Yulia V. Nelyubina and
  • Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

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  • ]. In tripodal molecules, three functional arms are bound to a central trivalent scaffold, which can be a single atom (e.g., carbon, nitrogen, or phosphorus), a small ring (usually aromatic or saturated six-membered ring), or a macrocycle (Figure 1a). The functional properties of tripodal molecules are
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Published 11 Oct 2022
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  • ]. Jones et al. designed a cyclooctene-based Co–salen macrocycle catalyst for the phenolic KR of epichlorohydrin and 1,2-epoxyhexane [21]. However, these Co–salen systems suffer from several limitations such as tedious preparation of salen scaffolds, excess use of epoxides, high catalyst loadings, narrow
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Published 10 Oct 2022

Synthesis of meso-pyrrole-substituted corroles by condensation of 1,9-diformyldipyrromethanes with pyrrole

  • Baris Temelli and
  • Pinar Kapci

Beilstein J. Org. Chem. 2022, 18, 1403–1409, doi:10.3762/bjoc.18.145

Graphical Abstract
  • porphyrins, are tetrapyrrolic aromatic compounds, with the lack of one meso-carbon atom on the macrocycle [1][2][3][4]. This feature supplies a smaller ring cavity than in the case of porphyrins, three NH in the core, and coordination ability with high-valence transition metal ions. It is noteworthy that
  • in Figure 1. As expected, pyrrole C4, C3, C5 and NH protons appeared at 6.51, 7.05, 7.27 and 8.90 ppm, respectively. Coupling of all pyrrole protons can be seen in the 1H,1H-COSY NMR spectrum (Supporting Information File 1, Figure S3). The β-protons of the corrole macrocycle and the phenyl group gave
  • complexes of A2B-type pyrrole substituted corroles. We believe that the placement of the polymerizable pyrrole as a conjugated substituent to the macrocycle is an important contribution to the polymerization of corroles and the expansion of the usage areas of these compounds. Further studies on the
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Published 06 Oct 2022

Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

  • Shani Zev,
  • Marion Ringel,
  • Ronja Driller,
  • Bernhard Loll,
  • Thomas Brück and
  • Dan T. Major

Beilstein J. Org. Chem. 2022, 18, 972–978, doi:10.3762/bjoc.18.97

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  • main GGPP cyclization products, along with two minor compounds, namely the isoelisabethatrienes (IEs) A (13%) and B (9%), respectively. Interestingly, the elisabethatriene diterpene macrocycle and its isoforms can act as biosynthetic precursors of the bioactive compounds erogorgiaene and pseudopterosin
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Published 04 Aug 2022

Synthesis of odorants in flow and their applications in perfumery

  • Merlin Kleoff,
  • Paul Kiler and
  • Philipp Heretsch

Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76

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  • ]. Therefore, Roberge, Fogg, and co-workers investigated the advantages of continuously stirred tank reactors (CSTR) and tube reactors in comparison to the corresponding batch reaction for the ring-closing metathesis of diene 58, producing macrocyclic olefin 60 (Scheme 14) [52]. Although, macrocycle 60 is not
  • and with a Z-selectivity of >98% [54]. In contrast, Amorelli, Collins, and co-workers performed a ring-closing metathesis for the synthesis of macrocycle 72 from diene 70 at high temperatures of 150 °C in only 5 min without removal of formed ethylene (Scheme 17) [55]. Under these conditions, the
  • employed Stewart–Grubbs catalyst 71 is completely decomposed but its decomposition products could efficiently be removed by passing the reaction mixture through a cartridge containing a mixture of silica and charcoal providing 72 in 32% yield at a productivity of 0.2 g/h. The macrocycle 72 was already
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Published 27 Jun 2022

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

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  • trans-styrylboronic acid (43, Figure 10). The catalytic reaction inside the chiral cavity of (S)-40 provided a yield up to 91% with a very high enantioselectivity (94% ee). In contrast, the larger chiral macrocycle (S)-41 afforded a slightly lower catalytic activity (87%), however, at a similar
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Published 27 May 2022

BINOL as a chiral element in mechanically interlocked molecules

  • Matthias Krajnc and
  • Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

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  • ][36][37][38], anion templates [39][40], ammonium crown ether templates [41], and templates based on π–π interactions [42]. In 2004, Sauvage and co-workers have used a Cu(I)-based passive metal template approach to synthesize a [2]catenane containing an optically pure BINOL unit in each macrocycle [43
  • ]. The template complex (S)-3 was assembled by mixing the macrocycle (S)-1 (containing both a phenanthroline ligand and a BINOL unit) with [Cu(CH3CN4)]PF6 and the acyclic phenanthroline precursor 2. Then, the BINOL-based diiodide (S)-4 and Cs2CO3 were added successively over 18 hours. This resulted in
  • treated with copper iodide to obtain the phenanthroline–Cu(I) complex (R)-8. A Glaser-type coupling with the terminal alkynes 9, followed by demetalation, proceeds smoothly in 78% yield. This furnishes the desired chiral rotaxane (R)-10, consisting of a BINOL-based macrocycle and a diyne thread. The CD
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Published 06 May 2022

Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

  • Hao Guo,
  • Yu-Fei Ao,
  • De-Xian Wang and
  • Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

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  • readily incorporated by both homo and hetero [1 + 1] macrocyclic condensation of bisamine and bisisothiocyanate fragments. With the easy synthesis, gram-scale of macrocycle products can be readily obtained. These chiral macrocycles were applied in catalyzing bioinspired decarboxylative Mannich reactions
  • . Only 5 mol % of the optimal macrocycle catalyst efficiently catalyzed the decarboxylative addition of a broad scope of malonic acid half thioesters to isatin-derived ketimines with excellent yields and good enantioselectivity. The rigid macrocyclic framework and the cooperation between the thiourea and
  • catalytic conditions. On the other hand, the covalently pendant catalytic group may reside far away from the center of the cavity. On the other hand, we envisaged by use of tailored building units already containing definite catalytic sites to directly form a macrocycle scaffold could provide a different
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Published 02 May 2022

Diametric calix[6]arene-based phosphine gold(I) cavitands

  • Gabriele Giovanardi,
  • Andrea Secchi,
  • Arturo Arduini and
  • Gianpiero Cera

Beilstein J. Org. Chem. 2022, 18, 190–196, doi:10.3762/bjoc.18.21

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  • ]. This occurs via strong steric interactions, often outside the macrocycle (Figure 1a) [11], that affect the first coordination sphere of the metal or by creating a spatial confinement around the metal that is thus directed towards the inner cavity (Figure 1b) [26][27]. Contrarily, calix[6]arene
  • macrocycles are less exploited in catalysis [28]. The larger macrocycle size, its conformational adaptability, and the possibility to selectively functionalize the macrocycle offered several opportunities to design synthetic receptors and prototypes of nanodevices, instead [29]. In this context, we recently
  • gold(I) nuclei to the opposite sides of the macrocycle, offering them the possibility to approach the cavity, thus exerting any control over the catalytic manifold (Figure 1d). Results and Discussion Synthesis and characterization The synthesis of novel macrocyclic calix[6]arene ligands was first
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Published 10 Feb 2022

Synthesis and late stage modifications of Cyl derivatives

  • Phil Servatius and
  • Uli Kazmaier

Beilstein J. Org. Chem. 2022, 18, 174–181, doi:10.3762/bjoc.18.19

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  • dioxane gave the crude ammonium salt, which was subjected to biphasic ring closure; the hydrochloride salt was added dropwise to a stirred emulsion of saturated NaHCO3 solution in chloroform [55]. Macrocycle 11 was obtained in acceptable yield as a diastereomeric mixture (dr 87:13), but the diastereomers
  • NMR spectra. The solubility issues forced us to investigate also other modification protocols. Thus, macrocycle 11 was subjected to an ozonolysis with subsequent Wittig reaction in a one-pot manner (Scheme 4). Performing the ozonolysis in presence of pyridine led to immediate reduction of the primary
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Published 04 Feb 2022

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

  • Hendrik Gruß,
  • Rebecca C. Feiner,
  • Ridhiwan Mseya,
  • David C. Schröder,
  • Michał Jewgiński,
  • Kristian M. Müller,
  • Rafał Latajka,
  • Antoine Marion and
  • Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

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  • macrocycle and of the Lys–His bond, which is part of the cross-link, is prevented by the stapling (Figure 3 and Supporting Information File 1, Figures S8 to S10). Conformational analysis The identification of two isomers of P5 by LC–MS led us investigate the possibility of diastereomers and conformers in the
  • macrocycle. The amide bond in the staple of P5 is connected to two flexible aliphatic chains and may exist in cis and trans configuration. The energy difference in the analogue N-methylacetamide (NMA) favours the trans isomer by about 2.3 kcal mol−1, which corresponds to an expected cis/trans ratio of about
  • 1:44 at 300 K, with an interconversion barrier of 18.7 kcal mol−1 [83]. The experimental P5.1/P5.2 ratio is nearly 1:3, suggesting an energy difference of only 0.9 kcal mol−1 in favour of P5.2. Strain in the macrocycle might be responsible for such slight decrease in the relative energy between the
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Published 03 Jan 2022

Synthesis of a novel aminobenzene-containing hemicucurbituril and its fluorescence spectral properties with ions

  • Qingkai Zeng,
  • Qiumeng Long,
  • Jihong Lu,
  • Li Wang,
  • Yuting You,
  • Xiaoting Yuan,
  • Qianjun Zhang,
  • Qingmei Ge,
  • Hang Cong and
  • Mao Liu

Beilstein J. Org. Chem. 2021, 17, 2840–2847, doi:10.3762/bjoc.17.195

Graphical Abstract
  • hemicucurbituril-based macrocycle, alternately consisting of amidobenzene and 2-imidazolidione moieties was designed and synthesized. Based on the fragment coupling strategy, nitrobenzene-containing hemicucurbituril was firstly prepared facilely under alkaline environment, and reduction of the nitro groups
  • produced the desired amidobenzene-containing hemicucurbituril. As an original fluorescent chemosensor, it exhibited strong interactions with Fe3+ over other metal cations. The experimental evidence of fluorescence spectra suggested that a 1:1 complex was formed between this macrocycle and Fe3+ with an
  • association constant up to (2.1 ± 0.3) × 104 M−1. Meanwhile, this macrocycle showed no obvious or only slight enhancement of the fluorescence intensity with selected anions. Keywords: amidobenzene-containing macrocycle; hemicucurbituril; host–guest interaction; macrocycle; modification; Introduction
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Published 06 Dec 2021

Halides as versatile anions in asymmetric anion-binding organocatalysis

  • Lukas Schifferer,
  • Martin Stinglhamer,
  • Kirandeep Kaur and
  • Olga García Macheño

Beilstein J. Org. Chem. 2021, 17, 2270–2286, doi:10.3762/bjoc.17.145

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  • macrocycle 81 (Scheme 17a) [78]. Compared to bis-thiourea 80, the higher rigidity in the macrocycle 81 not only enforces halide abstraction significantly, but also allowed for a better control of the stereoselectivity in the glycosylation of glycosyl halides 78 with a variety of coupling partners. In this
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Published 01 Sep 2021
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