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Search for "pyrrolidines" in Full Text gives 84 result(s) in Beilstein Journal of Organic Chemistry.

Copper–phenanthroline catalysts for regioselective synthesis of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions

  • Rupankar Paira,
  • Tarique Anwar,
  • Maitreyee Banerjee,
  • Yogesh P. Bharitkar,
  • Shyamal Mondal,
  • Sandip Kundu,
  • Abhijit Hazra,
  • Prakas R. Maulik and
  • Nirup B. Mondal

Beilstein J. Org. Chem. 2014, 10, 692–700, doi:10.3762/bjoc.10.62

Graphical Abstract
  • recent years, there have been many attempts to synthesize diversely modified pyrrolidines, both symmetric and asymmetric in nature. Several of these attempts involved 1,3-dipolar cycloaddition reactions involving azomethine ylides to give cycloadducts, which were further explored as potential antiviral
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Published 20 Mar 2014

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

  • Gijs Koopmanschap,
  • Eelco Ruijter and
  • Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

Graphical Abstract
  • ease of preparation via IMCRs [27][28][29]. First, the β-lactams will be described followed by five-membered rings varying from pyrrolidines to tetrazoles based amide bond isosteres. Examples of the six-membered rings showing peptide like-properties are the piperazines, homoprolines, dihydropyrimidones
  • to determine the biological activity of peptides and peptidomimetics,[50] and research towards such peptidic structures containing proline-analogues has received much attention [48]. In this part, multicomponent reactions to access pyrrolidines and other five-membered derivatives such as γ-lactams
  • , oxazoles, thiazoles and triazoles incorporated into peptide structures will be described. Pyrrolidines 2-substituted pyrrolidine-based dipeptide mimics were obtained from an Ugi-4CR followed by a Pd-catalyzed Sn2 cyclization as described by Banfi et al. [51] . Herein, the Ugi reaction provided a small
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Published 04 Mar 2014

Silver and gold-catalyzed multicomponent reactions

  • Giorgio Abbiati and
  • Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

Graphical Abstract
  • , aldehydes and alkenes in a three-component reaction based on the cascade imine formation, azomethine ylide generation and [3 + 2] cycloaddition reaction for the synthesis of pyrrolidines. However, the adopted method to induce chirality in the final products is rather dissimilar. Thus, in 2006 Garner’s group
  • reported the synthesis of highly functionalized pyrrolidines 77 in a MCR involving classical aliphatic aldehydes 74, chiral glycyl sultam 75 and activated alkenes 76 (Scheme 37) [96]. The Oppolzer’s camphorsultam, incorporated in the amine 75 by means of an amide linkage, plays two different roles. On the
  • tautomerization. Instead, an Ag(I) complex based on BINAP and AgSbF6 was employed as a catalyst for the enantioselective 1,3-dipolar cycloaddition reaction of azomethine ylides and alkenes for the synthesis of pyrrolidines 81 and 82 (Scheme 38) [97]. The reaction was developed mainly as a two-component reaction
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Published 26 Feb 2014

Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones

  • Murat Kucukdisli,
  • Dorota Ferenc,
  • Marcel Heinz,
  • Christine Wiebe and
  • Till Opatz

Beilstein J. Org. Chem. 2014, 10, 466–470, doi:10.3762/bjoc.10.44

Graphical Abstract
  • )nitriles can be used as versatile and readily accessible pronucleophiles, e.g. for the construction of γ-amino acids [32], pyrrolidines [33], as well as pyrroles [34][35]. If an additional conjugated double bond is present, the anions of α-(alkylideneamino)nitriles 3 can undergo an electrocyclic ring
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Published 24 Feb 2014

Aminofluorination of 2-alkynylanilines: a Au-catalyzed entry to fluorinated indoles

  • Antonio Arcadi,
  • Emanuela Pietropaolo,
  • Antonello Alvino and
  • Véronique Michelet

Beilstein J. Org. Chem. 2014, 10, 449–458, doi:10.3762/bjoc.10.42

Graphical Abstract
  • fluorination strategies by using Selectfluor as an electrophilic source of fluorine [24][25][26][27][28][29][30][31] can provide a powerful tool for building up nitrogen heterocycle derivatives. Fluorinated pyrrolidines [32] and fluorinated pyrazoles [33] have been synthesized from 1,ω-N-protected aminoalkynes
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Published 20 Feb 2014

Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines – development of a phosphite-driven cyclodehydration

  • Peter H. Huy,
  • Julia C. Westphal and
  • Ari M. P. Koskinen

Beilstein J. Org. Chem. 2014, 10, 369–383, doi:10.3762/bjoc.10.35

Graphical Abstract
  • ring expansions of 2-(α-hydroxyalkyl)pyrrolidines deduced to proline. 3. Based on the ring expansion of Cossy and Pardo [37], O´Brien [39] realized the synthesis of L-733,060 (80% ee). The 2-(α-hydroxyalkyl)pyrrolidine precursor was prepared from a protected pyrrolidine through sparteine-mediated
  • very good yields (>80%) to pyrrolidines, piperidines and furans 13a,b and 13d–h. The established cyclodehydration procedure only had to be slightly modified regarding the work up: As most of the products 13a,b and 13d–h are volatile, the crude reaction mixture was concentrated under reduced pressure
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Published 11 Feb 2014

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

  • Tatyana L. Pavlovskaya,
  • Fedor G. Yaremenko,
  • Victoria V. Lipson,
  • Svetlana V. Shishkina,
  • Oleg V. Shishkin,
  • Vladimir I. Musatov and
  • Alexander S. Karpenko

Beilstein J. Org. Chem. 2014, 10, 117–126, doi:10.3762/bjoc.10.8

Graphical Abstract
  • spirooxindoles. Recently, this route has become significant in combinatorial chemistry due to its process simplicity, mild conditions, atomic economy and extension of the scope of substrates. A large number of focused libraries of spirooxindolo pyrrolidines and pyrrolizidines containing a wide set of natural and
  • inhibitors there are compounds containing a pyrrolidine-2-one as a part of the spirocyclic system [34]. In the present work we report the synthesis of spirooxindolo pyrrolidines and pyrrolizidines by utilizing a 1,3-dipolar cycloaddition of hitherto uninvestigated acrylamides and aroylacrylic acids with
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Published 09 Jan 2014

Studies on the interaction of isocyanides with imines: reaction scope and mechanistic variations

  • Ouldouz Ghashghaei,
  • Consiglia Annamaria Manna,
  • Esther Vicente-García,
  • Marc Revés and
  • Rodolfo Lavilla

Beilstein J. Org. Chem. 2014, 10, 12–17, doi:10.3762/bjoc.10.3

Graphical Abstract
  • prepared in a straightforward manner. A part of the azetidine structure distinct scaffolds have been obtained from the interaction of different reactant combinations: α-aminoamides, α-aminoamidines, indoles, bis(imino)tetrahydroquinolines and tris(imino)pyrrolidines. Finally, a unified reaction mechanism
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Published 06 Jan 2014

Stereoselectively fluorinated N-heterocycles: a brief survey

  • Xiang-Guo Hu and
  • Luke Hunter

Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306

Graphical Abstract
  • transpires that this C–F…N+ interaction is a general effect which has also been observed in larger N-heterocycles, as discussed below. 3.2 Five-membered rings The C–F…N+ interaction can have a more dramatic impact on the conformations of pyrrolidines, since they are inherently more flexible than azetidines
  • the entire pyrrolidine ring by 180° relative to that of 9, and several different H-bonding contacts with the DNA as a result. In contrast with the strong charge–dipole effect evident in pyrrolidine 10 (Figure 3), another more subtle interaction is observed in neutral fluorinated pyrrolidines. For
  • axial conformers are preferred by a substantial ~5.0 kcal/mol over the equatorial conformers (not shown) [28][29]. This pioneering work constituted the original discovery of the C–F…N+ interaction which has already been discussed above in the context of azetidines and pyrrolidines. Interestingly, Lankin
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Published 29 Nov 2013

New developments in gold-catalyzed manipulation of inactivated alkenes

  • Michel Chiarucci and
  • Marco Bandini

Beilstein J. Org. Chem. 2013, 9, 2586–2614, doi:10.3762/bjoc.9.294

Graphical Abstract
  • amounts of the diene and nitrogen-based nucleophile. Analogously, Widenhoefer and Han developed the intramolecular addition of carbamates to terminal alkenes affording N-protected pyrrolidines and piperidines 21 (Scheme 7). Best conditions involved the use of a 1:1 mixture of [Au(I)] complex 20a and AgOTf
  • of alkenes catalyzed by Ph3PAuOTf (toluene, 85 °C, Scheme 8) [40]. In particular, primary and secondary sulfonamides reacted smoothly with mono and disubstituted alkenes delivering nitrogen compounds 22 and 23 with Markovnikov regioselectivity (Scheme 8a). Moreover, N-protected pyrrolidines 24 and 25
  • , efficiently (Scheme 9) [45]. When IPrAuCl (27) and AgOTf were mixed together in 1:1 ratio, the intramolecular exo-addition of N’-alkyl and N’-arylurea to primary or secondary olefins took place smoothly at room temperature to afford the variously substituted pyrrolidines 28 and piperidines 30 (Scheme 9a,b
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Published 21 Nov 2013

Synthetic scope and DFT analysis of the chiral binap–gold(I) complex-catalyzed 1,3-dipolar cycloaddition of azlactones with alkenes

  • María Martín-Rodríguez,
  • Luis M. Castelló,
  • Carmen Nájera,
  • José M. Sansano,
  • Olatz Larrañaga,
  • Abel de Cózar and
  • Fernando P. Cossío

Beilstein J. Org. Chem. 2013, 9, 2422–2433, doi:10.3762/bjoc.9.280

Graphical Abstract
  • submitted to different transformations. For example, it could be reduced to the corresponding pyrrolidines employing sodium cyanoborohydride in acidic media. In this reaction, a 1:1 mixture of 2,5-cis-pyrrolidine 13 and its 5-epimer 14 (2,5-trans) was isolated in good chemical yield (71%) (Scheme 7
  • maleimides. The general scope is not very wide but enantioselections obtained are quite good. Very interesting pyrrolidines with a trans-arrangement were obtained after hydrogenation of the pyrroline precursor. Chiral gold(I) complexes employed in 1,3-DC involving azomethine ylides. Positive non-linear
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Published 11 Nov 2013

The chemistry of amine radical cations produced by visible light photoredox catalysis

  • Jie Hu,
  • Jiang Wang,
  • Theresa H. Nguyen and
  • Nan Zheng

Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234

Graphical Abstract
  • pyrrolidines 43 and 47 (Scheme 12). Xiao also showed that the pyrrolidine ring of 43 could be further oxidized to a fused pyrrole 44 under the same photoredox conditions or by treatment with NBS. Both Ru(bpy)3Cl2 and Ir(bpy)(ppy)2 were found to be effective catalysts. A plausible mechanism for the 1,3-dipolar
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Published 01 Oct 2013

The rapid generation of isothiocyanates in flow

  • Marcus Baumann and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 1613–1619, doi:10.3762/bjoc.9.184

Graphical Abstract
  • pyrrolidines, isoxazolines and their derivatives [49][50][51][52]. We therefore considered that it should be possible to develop a mild and practical flow-based process to form isothiocyanates from the corresponding reactive nitrile oxide intermediates. Our strategy makes use of two immobilised reagents (a
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Published 08 Aug 2013

An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles

  • Alexandre Jean,
  • Jérôme Blanchet,
  • Jacques Rouden,
  • Jacques Maddaluno and
  • Michaël De Paolis

Beilstein J. Org. Chem. 2013, 9, 1480–1486, doi:10.3762/bjoc.9.168

Graphical Abstract
  • Ullmann-type condensation [8][9][10], the regioselective functionalization of pyrroles is less trivial when asymmetric substrates are targeted. An indirect solution, based on the construction of substituted pyrrolidines that oxidize into elaborated pyrroles, can be employed fruitfully [11][12]. We
  • recently described a one-pot organo-catalyzed synthesis of N-heteroarylmethylene pyrrolidines 4 [13] from readily available aldehydes 1 and imine 2 by a sequence of Mannich coupling [14][15][16][17][18][19][20][21][22][23][24], Wittig olefination with phosphonium 3, and proton-mediated hydroamination
  • silica gel before isomerization is more rewarding: following this route, the global yield for the whole process reaches 59% yield. Applying this procedure, various 2-heteroarylmethylenepyrrolidines 4b–h prepared from aldehydes 1b–h and imine 2a were exposed to DBU (1.1 equiv). Pleasingly, pyrrolidines 4b
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Published 24 Jul 2013

One-pot tandem cyclization of enantiopure asymmetric cis-2,5-disubstituted pyrrolidines: Facile access to chiral 10-heteroazatriquinanes

  • Ping-An Wang,
  • Sheng-Yong Zhang and
  • Henri B. Kagan

Beilstein J. Org. Chem. 2013, 9, 265–269, doi:10.3762/bjoc.9.32

Graphical Abstract
  • Moléculaire, Université Paris-Sud, 15 rue Georges Clemenceau, 91405 Orsay Cedex, France 10.3762/bjoc.9.32 Abstract A series of chiral 10-heteroazatriquinanes were synthesized from enantiopure asymmetric cis-2,5-disubstituted pyrrolidines through a one-pot tandem cyclization procedure. The structures and
  • complexes and calixiform scaffolds (Figure 1). Previously, we established a facile access to enantiopure asymmetric cis-2,5-disustituted pyrrolidines 4 from commercially available starting materials diethyl meso-2,5-dibromoadipate and (S)-(−)-1-phenylethylamine (Figure 2) [9]. The preparations of compounds
  • ][13][14] from compounds 4 through three steps, including reduction, debenzylation and cyclization (Scheme 1), but this failed. However, we have found a novel one-pot tandem cyclization of these enantiopure asymmetric cis-2,5-disubstituted pyrrolidines to produce chiral trisubstituted 10
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Published 07 Feb 2013

A quantitative approach to nucleophilic organocatalysis

  • Herbert Mayr,
  • Sami Lakhdar,
  • Biplab Maji and
  • Armin R. Ofial

Beilstein J. Org. Chem. 2012, 8, 1458–1478, doi:10.3762/bjoc.8.166

Graphical Abstract
  • range –10 < E < –5 were determined for iminium ions derived from cinnamaldehyde and common organocatalysts, such as pyrrolidines and imidazolidinones, by studying the rates of their reactions with reference nucleophiles. Iminium activated reactions of α,β-unsaturated aldehydes can, therefore, be
  • data in Figure 18 and Figure 19 now explains why the Jørgensen-Hayashi diphenylprolinol trimethylsilyl ether [81], the precursor of 32b, and structurally related pyrrolidines have previously been employed for catalyzing the reactions of aldehydes and ketones with weak electrophiles, such as β
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Published 05 Sep 2012

Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as iminosugar mimics

  • Marco Marradi,
  • Stefano Cicchi,
  • Francesco Sansone,
  • Alessandro Casnati and
  • Andrea Goti

Beilstein J. Org. Chem. 2012, 8, 951–957, doi:10.3762/bjoc.8.107

Graphical Abstract
  • with more complex and/or biologically relevant iminosugars. Keywords: calixarenes; cation-responsive system; dendrimers; iminosugars; multivalency; Introduction Polyhydroxylated pyrrolidines are one of the main classes of naturally occurring sugar mimics [1][2] and belong to the so-called iminosugars
  • open the way for the construction of more complex systems, decorated with biologically active polyhydroxylated pyrrolidines or piperidines. The synthesis of first- and second-generation iminosugar-based calixarene-dendrimers 2 and 3 (Figure 1) was addressed in order to prove the viability of such a
  • both as a dendrimeric building block and iminosugar model; its substitution at the hydroxy groups with more complex and biologically active iminosugars, such as polyhydroxylated pyrrolidines, would also allow the investigation of the corresponding calixarene dendrimers in interactions with enzymatic
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Published 26 Jun 2012

Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols

  • Marcin Jasiński,
  • Dieter Lentz and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2012, 8, 662–674, doi:10.3762/bjoc.8.74

Graphical Abstract
  • samarium diiodide leading to enantiopure acyclic aminopolyols. We also report on our attempts to convert these compounds into enantiopure hydroxylated pyrrolidine derivatives. Keywords: aminopolyols; carbohydrates; chiral auxiliaries; lithiated alkoxyallenes; 1,2-oxazines; pyrroles; pyrrolidines; samarium
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Published 30 Apr 2012

Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors

  • Davide Bini,
  • Francesca Cardona,
  • Matilde Forcella,
  • Camilla Parmeggiani,
  • Paolo Parenti,
  • Francesco Nicotra and
  • Laura Cipolla

Beilstein J. Org. Chem. 2012, 8, 514–521, doi:10.3762/bjoc.8.58

Graphical Abstract
  • scarcely characterised. Keywords: glycosidases inhibitors; iminosugars; nojirimycins; pyrrolidines; trehalases; Introduction Trehalase (EC3.2.1.28) is a glycosidase that catalyses trehalose (α-D-glucopyranosyl-α-D-glucopyranoside 1, Figure 1) [1][2][3] hydrolysis. It was found initially at the end of the
  • alkyl chain (Figure 3). These two compounds can help answer whether a medium-sized lipophylic chain can be accommodated into the catalytic site, and whether any difference could be due to the positioning of the chain itself. Only the “α-D-arabino-configured” pyrrolidines 20, 21 were considered here
  • , since preliminary data showed that “β-D-ribo-configured” pyrrolidines were not active at all (for details, see Enzyme assays). Chemical synthesis Based on the structure of lead compound 8 (Figure 2), which showed some selectivity towards insect trehalase from C.riparius [18], we envisaged the
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Published 05 Apr 2012

Continuous-flow enantioselective α-aminoxylation of aldehydes catalyzed by a polystyrene-immobilized hydroxyproline

  • Xacobe C. Cambeiro,
  • Rafael Martín-Rapún,
  • Pedro O. Miranda,
  • Sonia Sayalero,
  • Esther Alza,
  • Patricia Llanes and
  • Miquel A. Pericàs

Beilstein J. Org. Chem. 2011, 7, 1486–1493, doi:10.3762/bjoc.7.172

Graphical Abstract
  • subsequently applied to the synthesis of several biologically active compounds [18][19][20]. Proline is the most frequently used catalyst in α-aminoxylation reactions, but other catalytic species have also been developed and used. Chiral secondary amines, such as substituted pyrrolidines other than proline [21
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Published 31 Oct 2011

Amines as key building blocks in Pd-assisted multicomponent processes

  • Didier Bouyssi,
  • Nuno Monteiro and
  • Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

Graphical Abstract
  • ]. For instance, Balme and coworkers reported a Pd-catalyzed three-component assembly of highly functionalized 4-benzyl- and allyl-pyrrolidines 46 based on a combination of allylamines (in situ transformed to their sodium salts by treatment with NaH), gem-diactivated alkenes 45 as Michael acceptors, and
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Published 10 Oct 2011

Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles

  • Antoine Simonneau,
  • Pierre Garcia,
  • Jean-Philippe Goddard,
  • Virginie Mouriès-Mansuy,
  • Max Malacria and
  • Louis Fensterbank

Beilstein J. Org. Chem. 2011, 7, 1379–1386, doi:10.3762/bjoc.7.162

Graphical Abstract
  • the elucidation of the mechanism and Selectfluor was suggested to play the double role of promoting the oxidation of gold(I) to a gold(III) active species and also the electrophilic fluorination of the enamine intermediates. Keywords: cycloisomerization reactions; fluorinated pyrrolidines; gold
  • summarized in Table 1. The reaction of 1a in the presence of commercially available Ph3PAuCl (5 mol %) and Selectfluor (1.1 equiv) in acetonitrile at rt afforded an inseparable mixture of pyrrolidines 3a in 75% yield and 4a in 17% yield (Table 1, entry 1). Difluoro derivative 4a was isolated as a single
  • fluorinated pyrrolidines 3a, 4a and 2-pyrroline 5a are unknown and could be interesting building blocks for organic synthesis. Following the previous catalyst screening, we stuck with the use of PPh3AuCl as the catalyst and next investigated the effect of the concentration of 1a and the stoichiometry of
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Published 07 Oct 2011

Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters

  • Satish S. More,
  • T. Krishna Mohan,
  • Y. Sateesh Kumar,
  • U. K. Syam Kumar and
  • Navin B. Patel

Beilstein J. Org. Chem. 2011, 7, 831–838, doi:10.3762/bjoc.7.95

Graphical Abstract
  • substituted novel pyrroline derivatives have been synthesized by this methodology and the products can be used as key intermediates in the synthesis of substituted pyrrolines, pyrroles and pyrrolidines. Keywords: 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates; aziridine; N
  • materials in the preparation of substituted pyrroles, pyrrolines and pyrrolidines. The pyrrolines as well as pyrrolidines with substitution at the 2-position are important structural units in many natural products. A few of the natural products that contain 2-substituted pyrroline and 2-substituted
  • at 100–110 °C for a period of 12 h, the mono ester 24 was isolated as the major product in 65% yield along with 10% of unreacted starting material and 10% of pyrroline derivative 23 (Scheme 3). The imine bond reduction in pyrrolines to pyrrolidines can be carried out by established procedures in
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Published 20 Jun 2011

Synthetic applications of gold-catalyzed ring expansions

  • David Garayalde and
  • Cristina Nevado

Beilstein J. Org. Chem. 2011, 7, 767–780, doi:10.3762/bjoc.7.87

Graphical Abstract
  • starting from allenyl cyclobutanols [23]. 1.2 Cyclopropylmethanols Cyclopropyl methanols can be used, alternatively, as pre-electrophiles in gold-catalyzed reactions. In 2008 Chan and co-workers developed an efficient synthetic route to pyrrolidines via a tandem amination/ring expansion of these substrates
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Published 07 Jun 2011

Metathesis access to monocyclic iminocyclitol-based therapeutic agents

  • Ileana Dragutan,
  • Valerian Dragutan,
  • Carmen Mitan,
  • Hermanus C.M. Vosloo,
  • Lionel Delaude and
  • Albert Demonceau

Beilstein J. Org. Chem. 2011, 7, 699–716, doi:10.3762/bjoc.7.81

Graphical Abstract
  • ; iminocyclitols; natural products; olefin metathesis; Ru-alkylidene catalysts; Review Introduction Synthetic and natural polyhydroxylated N-heterocyclic compounds (pyrrolidines, piperidines, piperazines, indolizines, etc., and higher homologues), commonly referred to as azasugars, iminosugars or iminocyclitols
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Published 27 May 2011
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