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Search for "organocatalysts" in Full Text gives 176 result(s) in Beilstein Journal of Organic Chemistry.

1-n-Butyl-3-methylimidazolium-2-carboxylate: a versatile precatalyst for the ring-opening polymerization of ε-caprolactone and rac-lactide under solvent-free conditions

  • Astrid Hoppe,
  • Faten Sadaka,
  • Claire-Hélène Brachais,
  • Gilles Boni,
  • Jean-Pierre Couvercelle and
  • Laurent Plasseraud

Beilstein J. Org. Chem. 2013, 9, 647–654, doi:10.3762/bjoc.9.73

Graphical Abstract
  • (DMC) with imidazole derivatives, making them very attractive and accessible compounds [35]. Therefore, they found applications as ligands in organometallic catalysis [36][37][38][39][40][41], as precursors of halide-free ionic liquids [42][43][44][45], and as organocatalysts in reactions involving
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Published 03 Apr 2013

NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes

  • Lennart Möhlmann,
  • Stefan Ludwig and
  • Siegfried Blechert

Beilstein J. Org. Chem. 2013, 9, 602–607, doi:10.3762/bjoc.9.65

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  • of aldehydes to the corresponding acids or esters. The reaction proceeds under metal-free conditions by using N-heterocyclic carbenes as organocatalysts in combination with environmentally friendly oxygen as the terminal oxidation agent. Keywords: aerobic oxidation; chemoselective oxidation; metal
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Published 22 Mar 2013

Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions

  • Matthias Leven,
  • Jörg M. Neudörfl and
  • Bernd Goldfuss

Beilstein J. Org. Chem. 2013, 9, 155–165, doi:10.3762/bjoc.9.18

Graphical Abstract
  • vitamin K antagonist, and the dissimilar activity of the enantiomers is well documented in the literature [30][31][32]. The organocatalytic synthesis of warfarin has already been tested with several organocatalysts. Diphenylglycinol derivatives and derivatives of 1,2-diphenylethane-1,2-diamine provided
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Published 23 Jan 2013

Mechanochemistry assisted asymmetric organocatalysis: A sustainable approach

  • Pankaj Chauhan and
  • Swapandeep Singh Chimni

Beilstein J. Org. Chem. 2012, 8, 2132–2141, doi:10.3762/bjoc.8.240

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  • amplified in recent times. In this regard, catalytic asymmetric synthesis involving the use of chiral organocatalysts has emerged as a powerful tool from the infancy to the maturity of asymmetric organocatalysis [13][14][15][16][17][18][19][20][21][22][23][24][25][26]. The use of organocatalysts for
  • . Organocatalyts also provide an insight into biological catalytic processes, as a number of these catalysts work by the phenomenon of enzyme mimicry. These advantages of chiral organocatalysts also meet many of the requirements of green chemistry [27]. Recently developed, organocatalytic asymmetric
  • various bioactive molecules [28]. Among different organocatalysts used for asymmetric aldol reactions, proline and its derivatives emerged as powerful catalysts for the enamine activation of donor aldehyde or ketone. Bolm’s group reported a solvent-free asymmetric organocatalytic aldol reaction under ball
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Published 06 Dec 2012

Design and synthesis of a photoswitchable guanidine catalyst

  • Philipp Viehmann and
  • Stefan Hecht

Beilstein J. Org. Chem. 2012, 8, 1825–1830, doi:10.3762/bjoc.8.209

Graphical Abstract
  • ]. Metal-based catalysts as well as organocatalysts have been widely studied in the ROP of lactide [15]. Guanidines, and especially 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), have proven to be very powerful in this context (Scheme 1) [16]. However, due to the discussion of several polymerization mechanisms
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Published 24 Oct 2012

Automated three-component synthesis of a library of γ-lactams

  • Erik Fenster,
  • David Hill,
  • Oliver Reiser and
  • Jeffrey Aubé

Beilstein J. Org. Chem. 2012, 8, 1804–1813, doi:10.3762/bjoc.8.206

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  • addition of enolizable aldehydes to maleimides in the original method suggested the possibility of producing chiral γ-lactams through the use of a chiral proline-like organocatalysts. In fact, Córdova and co-workers have previously established a protocol for such a process [13]. Based on this initial
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Published 19 Oct 2012

Imidazolinium and amidinium salts as Lewis acid organocatalysts

  • Oksana Sereda,
  • Nicole Clemens,
  • Tatjana Heckel and
  • René Wilhelm

Beilstein J. Org. Chem. 2012, 8, 1798–1803, doi:10.3762/bjoc.8.205

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  • and amidinium salts as soft Lewis acid organocatalysts is described. These salts were suitable catalysts for the activation of unsaturated thioesters in a Diels–Alder reaction and in the ring opening of thiiranes and epoxides. The products were isolated in good yields. The mild catalysts did not cause
  • that bis-imidazolinium salts can be applied as Lewis acid organocatalysts to activate a thiocarbonyl group. Next, the behavior of these salts in the ring opening of a thiirane was explored. No activity was observed with salt 9 in the ring opening with aniline. Therefore, the more active bis
  • transformed directly by anion metathesis to the salt 21. Conclusion It was possible to prepare new metal-free Lewis acids containing bis-imidazolinium cations and investigate the salts as organocatalysts. Although with enantiopure chiral salts no enantiomeric excess was observed, it was shown for the first
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Published 18 Oct 2012

Asymmetric desymmetrization of meso-diols by C2-symmetric chiral 4-pyrrolidinopyridines

  • Hartmut Schedel,
  • Keizo Kan,
  • Yoshihiro Ueda,
  • Kenji Mishiro,
  • Keisuke Yoshida,
  • Takumi Furuta and
  • Takeo Kawabata

Beilstein J. Org. Chem. 2012, 8, 1778–1787, doi:10.3762/bjoc.8.203

Graphical Abstract
  • pyrrolidinopyridine framework as a catalytic site. Some of these organocatalysts effectively promoted asymmetric desymmetrization of meso-diols via enantioselective acylation. Keywords: acylation; desymmetrization; hydrogen bond; meso-diol; nucleophilic catalyst; organocatalysis; Introduction Since the pioneering
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Published 17 Oct 2012

Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives

  • Zhi-Cong Geng,
  • Jian Chen,
  • Ning Li,
  • Xiao-Fei Huang,
  • Yong Zhang,
  • Ya-Wen Zhang and
  • Xing-Wang Wang

Beilstein J. Org. Chem. 2012, 8, 1710–1720, doi:10.3762/bjoc.8.195

Graphical Abstract
  • /hemiacetal sequence with chiral or achiral secondary amines as organocatalysts. Thus, a series of achiral pyrazolidine derivatives were obtained with good yields (up to 90%) and high diastereoselectivities (>20:1) with pyrrolidine as an organocatalyst, and enantioenriched pyrazolidines are also achieved with
  • investigated in the presence of several common secondary amines 1a–f as organocatalysts in chloroform. Pyrrolidine (1c) turned out to be an effective catalyst and di-tert-butyl hydrazine-1,2-dicarboxylate (2c) was a potent donor (see Table S1 in the Supporting Information File 1). When di-tert-butyl hydrazine
  • -Michael/hemiacetal reaction. Initially, a series of readily available chiral organocatalysts 1g–o were chosen and investigated for the domino aza- Michael/hemiacetal reaction of disubstituted hydrazine 2c and 4-nitrocinnamaldehyde (3a) under catalytic loading of 20 mol % in CH2Cl2 at room temperature. The
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Published 09 Oct 2012

Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines

  • Chittaranjan Bhanja,
  • Satyaban Jena,
  • Sabita Nayak and
  • Seetaram Mohapatra

Beilstein J. Org. Chem. 2012, 8, 1668–1694, doi:10.3762/bjoc.8.191

Graphical Abstract
  • thiochromenes; and (3) Organocatalytic aza-Michael reactions to access functionalized 1,2-dihydroquinolines, using chiral proline and its derivatives (Figure 2), chiral bifunctional thioureas, cinchona alkaloids and other organocatalysts (Figure 3). For each reaction, the initial screening result of various
  • organocatalysts with their percentage of conversion (% yield) and enantiomeric excess (ee) is presented in tabular form, and the best catalyst is used for the given individual scheme. Review 1 Organocatalytic oxa-Michael additions to access functionalized chromenes 1.1. Reactions of 2-hydroxybenzaldehydes with
  • pyrrolidine-triazole-based C2 symmetric organocatalysts XXVIIa was reported by Sankararaman et al. [61] for the asymmetric synthesis of nitrochromenes 30 (Scheme 15). The reaction gave poor enantioselectivities both in toluene (15% ee) and in DMF (24% ee). In 2010, Das et al. [62] reported an organocatalytic
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Published 04 Oct 2012

Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity

  • Tatyana E. Shubina,
  • Matthias Freund,
  • Sebastian Schenker,
  • Timothy Clark and
  • Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2012, 8, 1485–1498, doi:10.3762/bjoc.8.168

Graphical Abstract
  • ; Introduction In recent years bifunctional compounds have found frequent applications as organocatalysts in modern synthetic organic chemistry [1][2][3][4][5][6][7][8]. Over the past decade, different catalytic methodologies have been reported that use chiral thiourea-based bifunctional molecules [9][10][11][12
  • ][13]. In particular, remarkable progress has been made in the development of secondary and tertiary amine-thiourea bifunctional organocatalysts for a great number of useful transformations [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. Recently, the Tsogoeva
  • group and that of Jacobsen reported the first successful application of primary amine-thiourea organocatalysts with the synchronous dual activation of a nucleophile and an electrophile in nitro-Michael addition reactions [36][37][38][39][40][41][42]. Bifunctional organocatalysts that contain both a
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Published 07 Sep 2012

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
  • settled by studying the reactivities of independently synthesized intermediates. Kinetic investigations of the reactions of N-heterocyclic carbenes (NHCs) with benzhydrylium ions showed that they have similar nucleophilicities to common organocatalysts (e.g., PPh3, DMAP, DABCO) but are much stronger (100
  • ]. Quantitative aspects of N-heterocyclic carbene (NHC) catalysis As the following discussion will focus on the difference between the kinetic term “nucleophilicity” and the thermodynamic term “Lewis basicity”, let us first illustrate this aspect by comparing the behavior of two well-known organocatalysts, 1,4
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Published 05 Sep 2012

Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones

  • Sergei Žari,
  • Tiiu Kailas,
  • Marina Kudrjashova,
  • Mario Öeren,
  • Ivar Järving,
  • Toomas Tamm,
  • Margus Lopp and
  • Tõnis Kanger

Beilstein J. Org. Chem. 2012, 8, 1452–1457, doi:10.3762/bjoc.8.165

Graphical Abstract
  • investigated the organocatalytic approach to the asymmetric desymmetrization of the title compounds with malonates. Three types of organocatalysts providing noncovalent interactions were used for this purpose: Cinchona alkaloids (I–V), thiourea derivatives (VI, VII) and squaramide derivatives (VIII, IX
  • yields (up to 99%) and in high enantioselectivities (up to 93%). This enantioselective 1,4-addition to unsaturated 1,4-diketones affords valuable intermediates for further synthetic transformations. The conjugated addition to unsaturated 1,4-diketone 1. Organocatalysts screened. Proposed transition state
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Published 04 Sep 2012

Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis

  • Marcus Frings,
  • Isabelle Thomé and
  • Carsten Bolm

Beilstein J. Org. Chem. 2012, 8, 1443–1451, doi:10.3762/bjoc.8.164

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  • Marcus Frings Isabelle Thome Carsten Bolm Institut für Organische Chemie, Landoltweg 1, RWTH Aachen University, 52074 Aachen, Germany 10.3762/bjoc.8.164 Abstract For the first time, chiral sulfoximine derivatives have been applied as asymmetric organocatalysts. In combination with a thiourea-type
  • backbone the sulfonimidoyl moiety leads to organocatalysts showing good reactivity in the catalytic desymmetrization of a cyclic meso-anhydride and moderate enantioselectivity in the catalytic asymmetric Biginelli reaction. Straightforward synthetic routes provide the newly designed thiourea-sulfoximine
  • reactions in a highly enantioselective manner has no end in sight. In this context, thiourea-based organocatalysts have caught significant attention due to their ability to activate substrates through hydrogen-bonding [42][43][44][45][46][47]. Usually, these chiral thioureas are classified into several
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Published 03 Sep 2012

Cation affinity numbers of Lewis bases

  • Christoph Lindner,
  • Raman Tandon,
  • Boris Maryasin,
  • Evgeny Larionov and
  • Hendrik Zipse

Beilstein J. Org. Chem. 2012, 8, 1406–1442, doi:10.3762/bjoc.8.163

Graphical Abstract
  • : "MP2-5") reproduce results obtained at the G3 level within 4.0 kJ/mol for selected small and medium-sized organocatalysts [5]. For pyridine (1) the MCA value obtained with this model amounts to MCA(1) = +518.7 kJ/mol, which is only 0.5 kJ/mol lower than the G3 value. The following discussion will thus
  • 109 times more nucleophilic. This is in agreement with the MCA values for 341 and 342, which are approx. 50 kJ/mol higher compared to the value of 334. However, including other typical organocatalysts such as PPh3 (89), DMAP (54), and DBU (60) in the comparison of MCA- and N-values, Mayr et al. note
  • collected in Table 9. The benzhydryl cation affinities (BHCA) of weak nucleophiles like ammonia (344) and phosphane (343) are less than 100 kJ/mol and thus much smaller than the respective MCA values. In contrast, often used organocatalysts like 4-dimethylaminopyridine (54), PPY (56), and PPh3 (89) possess
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Published 31 Aug 2012

Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels–Alder reactions

  • Stefan Bräse,
  • Nicole Volz,
  • Franziska Gläser and
  • Martin Nieger

Beilstein J. Org. Chem. 2012, 8, 1385–1392, doi:10.3762/bjoc.8.160

Graphical Abstract
  • fine chemicals, were either transition-metal complexes or enzymes. In the past few years, however, organocatalysis has emerged as an alternative approach for the catalytic production of enantiomerically pure organic compounds [15][16]. These organocatalysts have several important advantages. They are
  • , organocatalytic methods are especially attractive for the preparation of compounds that do not tolerate metal contamination, e.g., active pharmaceutical ingredients. MacMillan’s imidazolidinone-based organocatalysts are general catalysts for a variety of asymmetric transformations. The first highly
  • performed a catalyst screening with the previously synthesized imidazolidinone catalysts 15 to study their asymmetric induction (Scheme 5). As starting material we used compound 17 with the THC-typical pentyl side chain. The results are summarized in Table 5. The used organocatalysts, having a (S
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Published 28 Aug 2012

Organocatalytic C–H activation reactions

  • Subhas Chandra Pan

Beilstein J. Org. Chem. 2012, 8, 1374–1384, doi:10.3762/bjoc.8.159

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  • non-asymmetric and asymmetric C–H activation reactions mediated by organocatalysts are discussed in this review. Keywords: asymmetric; C–H activation; non-asymmetric; organocatalysis; organocatalytic; Introduction C–H activation reactions have recently been found to be a powerful method for the
  • activation is well-known in the literature [26][27][28][29][30]. Stoichiometric amounts of a radical source, such as tributyltin hydride and tris(trimethylsilyl)silicon hydride [31], or irradiation [32] were also utilized for biaryl synthesis from unactivated arenes. However, organocatalysts have not been
  • ongoing. Conclusion In summary, this review highlights the recent developments of organocatalytic C–H activation reactions. Organocatalysts have been involved in 1,5-hydride shift and decarboxylative/non-decarboxylative redox-amination processes. Asymmetric organocatalytic C–H activation reactions have
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Published 27 Aug 2012

Organocatalysis

  • Benjamin List

Beilstein J. Org. Chem. 2012, 8, 1358–1359, doi:10.3762/bjoc.8.156

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  • -molecular-weight organic compounds, in which a metal is not part of the active principle. Organocatalysts donate or remove electrons or protons as their activation mode, hence defining four distinct subareas: Lewis base and Lewis acid catalysis on the one hand, and Brønsted base and Brønsted acid catalysis
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Published 23 Aug 2012

Asymmetric one-pot sequential Friedel–Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme

  • Kengo Akagawa,
  • Ryota Umezawa and
  • Kazuaki Kudo

Beilstein J. Org. Chem. 2012, 8, 1333–1337, doi:10.3762/bjoc.8.152

Graphical Abstract
  • they often have chiral carbon chains attached to indole rings. A Friedel–Crafts-type asymmetric alkylation (FCAA) to indoles is a versatile method for synthesizing such chiral indole derivatives. To date, a number of FCAA reactions by either metal catalysts or organocatalysts have been reported [4][5
  • ][6][7][8][9][10][11]. Especially because organocatalysts have been demonstrated to possess a high feasibility for sequential reactions [12][13][14][15][16], it is expected that a sequential reaction including an organocatalytic FCAA step could provide highly functionalized indole compounds [17][18
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Published 17 Aug 2012

Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones

  • Chunhui Jiang,
  • Fangrui Zhong and
  • Yixin Lu

Beilstein J. Org. Chem. 2012, 8, 1279–1283, doi:10.3762/bjoc.8.144

Graphical Abstract
  • electrophiles, including aldehydes, ketones, imines, activated alkenes and azodicarboxylates, have been employed as electrophiles in the presence of metal [21][22][23][24][25] or organocatalysts [26][27][28][29][30][31][32][33][34][35][36]. To provide a practical solution to the low reactivity associated with
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Published 13 Aug 2012

Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters

  • Wen-Bin Yi,
  • Xin Huang,
  • Zijuan Zhang,
  • Dian-Rong Zhu,
  • Chun Cai and
  • Wei Zhang

Beilstein J. Org. Chem. 2012, 8, 1233–1240, doi:10.3762/bjoc.8.138

Graphical Abstract
  • supported cinchona alkaloids have been developed as recyclable chiral promoters or organocatalysts. Among them, the Cahard group developed soluble polymer- and ionic-liquid-supported cinchona alkaloids for electrophilic fluorination [21][22]. The Fache and Soόs groups developed fluorous tag-attached
  • cinchona alkaloids for catalytic Diels–Alder reactions [23][24]. Introduced in this paper is a new fluorous cinchona alkaloid ester for flourination of β-ketoesters. It is part of our recent effort on the development of recyclable fluorous reagents and organocatalysts for asymmetric synthesis [25][26][27
  • organocatalysts and reagents can be readily recovered by F-SPE [19][20]. In the current work, upon completion of the fluorination reaction, a base such as aqueous NaOH or KOH was added to the reaction mixture to convert the cinchona alkaloid/Selectfluor complex to free cinchona alkaloid. The organic phase was
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Published 03 Aug 2012

Combined bead polymerization and Cinchona organocatalyst immobilization by thiol–ene addition

  • Kim A. Fredriksen,
  • Tor E. Kristensen and
  • Tore Hansen

Beilstein J. Org. Chem. 2012, 8, 1126–1133, doi:10.3762/bjoc.8.125

Graphical Abstract
  • immobilization of Cinchona organocatalysts using thiol–ene chemistry, in which catalyst immobilization and bead polymerization is combined in a single step. A solution of azo initiator, polyfunctional thiol, polyfunctional alkene and an unmodified Cinchona-derived organocatalyst in a solvent is suspended in
  • water and copolymerized on heating by thiol–ene additions. The resultant spherical and gel-type polymer beads have been evaluated as organocatalysts in catalytic asymmetric transformations. Keywords: asymmetric catalysis; Cinchona derivatives; organocatalysis; polymerization; thiol–ene reaction
  • ; Introduction Polymer-supported chiral organocatalysts have emerged as a rapidly expanding field of research in recent years [1], in part due to the traditionally emphasized advantages of polymeric immobilization (facilitated separation and recovery procedures, recycling etc.), but perhaps even more due to the
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Published 20 Jul 2012

Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts

  • Saet Byeol Woo and
  • Dae Young Kim

Beilstein J. Org. Chem. 2012, 8, 699–704, doi:10.3762/bjoc.8.78

Graphical Abstract
  • organocatalysts is described. This reaction afforded the chiral functionalized naphthoquinones in high yields (81–95%) and excellent enantioselectivities (91–98% ee) under low catalyst loading (1 mol %). Keywords: asymmetric catalysis; Michael addition; 1,4-naphthoquinones; nitroalkenes; organocatalysis
  • , bifunctional tertiary-amine thioureas, thiophosphorodiamides, and squaramide-based organocatalysts [34][35][36]. Findings In the framework of our research program for the development of synthetic methods for the enantioselective construction of stereogenic carbon centers [37][38][39][40][41][42], we recently
  • reported the enantioselective Michael addition of active methines to nitroalkenes [43][44]. Herein, we describe the direct enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinone with nitroalkenes, catalyzed by bifunctional organocatalysts (Figure 1) that bear both central and axial chiral
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Published 07 May 2012

Kinetics and mechanism of vanadium catalysed asymmetric cyanohydrin synthesis in propylene carbonate

  • Michael North and
  • Marta Omedes-Pujol

Beilstein J. Org. Chem. 2010, 6, 1043–1055, doi:10.3762/bjoc.6.119

Graphical Abstract
  • and β-amino alcohols [2] (Scheme 1). Asymmetric cyanohydrin synthesis can be achieved by the use of a suitable chiral catalyst, and a wide range of catalysts have been found to catalyse this reaction including enzymes [3][4], organocatalysts [5][6] and metal-based catalysts [1]. All of the most
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Published 03 Nov 2010

The C–F bond as a conformational tool in organic and biological chemistry

  • Luke Hunter

Beilstein J. Org. Chem. 2010, 6, No. 38, doi:10.3762/bjoc.6.38

Graphical Abstract
  • of functional molecules that exploit these conformational effects will then be presented, drawing from a diverse range of molecules including pharmaceuticals, organocatalysts, liquid crystals and peptides. Keywords: conformation; functional molecules; organofluorine chemistry; stereochemistry
  • bound to TRPV1 since both enantiomers can approximate this conformation equally well [31]. This interpretation is in agreement with a previous study which made inferences from X-ray crystallography of a related receptor [32]. Organocatalysts So far we have seen that the C–F bond can be a valuable tool
  • for medicinal chemists seeking to control the molecular conformation of drugs and bioprobes. This section will show that the C–F bond is also emerging as a useful tool in the field of catalysis. Recent reports have shown that organocatalysts can be conformationally “fine-tuned” by fluorine
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Published 20 Apr 2010
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