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Search for "gold-catalyzed" in Full Text gives 101 result(s) in Beilstein Journal of Organic Chemistry.

Gold(I)-catalyzed enantioselective cycloaddition reactions

  • Fernando López and
  • José L. Mascareñas

Beilstein J. Org. Chem. 2013, 9, 2250–2264, doi:10.3762/bjoc.9.264

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  • the capacity to transfer asymmetry [12]. A number of strategies to tackle this problem have been developed, most of them based on the use of a new type of chiral gold complexes. This resulted in a number of gold-catalyzed enantioselective transformations in the past years, including hydrogenations
  • intermediates Gold–carbene species are frequent intermediates in gold-catalyzed reactions, in particular those involving alkynes [33][34][35][36][37]. Gold(I) catalysts bind chemoselectively to C–C triple bonds, promoting the attack of different types of nucleophiles on these electrophilic species. Depending on
  • intermediates of type A can engage in different types of cycloaddition reactions with diverse C–C unsaturated systems. Here, we discuss the systems for which an enantioselective variant has been developed. In 2005, Toste and coworkers described one of the first gold-catalyzed enantioselective processes that
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Published 30 Oct 2013

Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes

  • Ana M. Sanjuán,
  • Alberto Martínez,
  • Patricia García-García,
  • Manuel A. Fernández-Rodríguez and
  • Roberto Sanz

Beilstein J. Org. Chem. 2013, 9, 2242–2249, doi:10.3762/bjoc.9.263

Graphical Abstract
  • minor amounts of XI were also obtained [23] (Scheme 2). Following our interest in the development of new gold-catalyzed reactions [24][25][26][27][28][29][30][31], in this context we thought that it could be interesting to study if the cyclization of easily available compounds 1 bearing an internal
  • catalyst and reaction conditions on the hydroxycyclization of 1a. 6-Endo vs 5-exo cyclization.a Synthesis of 2-(1,2-dihydro-3-substituted-naphthalen-2-yl)propan-2-ol derivatives 7 by gold-catalyzed 6-endo hydroxycyclization of enynes 1.a Supporting Information Experimental procedures and spectroscopic
  • to cyclopenta[b]naphthalenes VIII or, alternatively, a 6-endo cyclization to bicyclo[4.1.0]hept-4-enes like IX [18][19] (Scheme 1). In the case that MeOH is present a 5-exo methoxycyclization is observed, e.g., in the formation of X resembling the behaviour of I [16][20]. In addition, the gold
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Published 29 Oct 2013

Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

  • Yin-wei Sun,
  • Qin Xu and
  • Min Shi

Beilstein J. Org. Chem. 2013, 9, 2224–2232, doi:10.3762/bjoc.9.261

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  • decades [1][2][3][4][5][6][7][8][9]. In the past few years, reports on gold-catalyzed organic transformations have increased substantially [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29]. Homogeneous gold catalysis has proven to be a powerful tool in organic synthesis
  • PhMgBr. Its structure was also confirmed by the X-ray crystal structure diffraction (Figure SI-1 in Supporting Information File 1). The catalytic activities of these gold complexes were examined by the gold-catalyzed asymmetric intramolecular hydroamination of olefin 24 tethered with a NHTs functional
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Published 28 Oct 2013

Synthesis, characterization and luminescence studies of gold(I)–NHC amide complexes

  • Adrián Gómez-Suárez,
  • David J. Nelson,
  • David G. Thompson,
  • David B. Cordes,
  • Duncan Graham,
  • Alexandra M. Z. Slawin and
  • Steven P. Nolan

Beilstein J. Org. Chem. 2013, 9, 2216–2223, doi:10.3762/bjoc.9.260

Graphical Abstract
  • catalysts in gold-catalyzed processes [1][2][3][4][5][6][7]. This has led several research groups to investigate general, green and straightforward methodologies for the synthesis of organogold complexes. We have focused on the synthesis and study of transition metal complexes bearing N-heterocyclic carbene
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Published 28 Oct 2013

Gold-catalyzed glycosidation for the synthesis of trisaccharides by applying the armed–disarmed strategy

  • Abhijeet K. Kayastha and
  • Srinivas Hotha

Beilstein J. Org. Chem. 2013, 9, 2147–2155, doi:10.3762/bjoc.9.252

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  • -catalyzed glycosidations [22][23][24][25][26][27][28]. Propargyl mannopyranosides as glycosyl donors are ideal for investigating armed–disarmed strategies for the synthesis of oligosaccharides, because the gold-catalyzed glycosidation proceeds in a highly 1,2-trans diastereoselective fashion [22
  • ]. Accordingly, the armed mannosyl donor 1 was allowed to react with the disarmed aglycon 2, under the standard conditions for a gold-catalyzed glycosidation (AuBr3, CH3CN, 70 °C), to observe the formation of disaccharide 3, in which the propargyl substitution is disarmed due to the presence of benzoates
  • mannoside 9 (9%) and lactol 10 (6%), which indicated the hydrolysis of the primary benzyl ether. The gold-catalyzed hydrolysis of benzyl ethers was not observed in the case of non-carbohydrate benzyl ether 11 (Scheme 3). For example, per-O-benzylated glycerol 11 did not show any benzyl deprotection, whereas
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Published 18 Oct 2013

Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives

  • Pablo Morán-Poladura,
  • Eduardo Rubio and
  • José M. González

Beilstein J. Org. Chem. 2013, 9, 2120–2128, doi:10.3762/bjoc.9.249

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  • aryl (3-iodoprop-2-yn-1-yl) ethers relying on the power of gold(I) catalysis, as depicted in Scheme 1 entry d. Herein, we report a new strategy to carry out this transformation. Results and Discussion In a previous work on gold-catalyzed cyclization reactions of N-(3-iodoprop-2-ynyl)-N-tosylanilines
  • , the reported gold-catalyzed cyclization opens up a versatile approach to the synthesis of elusive 4-unsubstituted-3-iodo-2H-chromenes. This transformation uses common starting materials. The resulting protocol is compatible with a significant variety of functional groups and can be easily conducted on
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Published 16 Oct 2013

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

  • Amit Kumar,
  • Dipak D. Vachhani,
  • Sachin G. Modha,
  • Sunil K. Sharma,
  • Virinder S. Parmar and
  • Erik V. Van der Eycken

Beilstein J. Org. Chem. 2013, 9, 2097–2102, doi:10.3762/bjoc.9.246

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  • adducts which are subjected to a cationic gold-catalyzed diastereoselective domino cyclization to furnish diversely substituted spiroindolines. All the reactions run via an exo-dig attack in the hydroarylation step followed by an intramolecular diastereoselective trapping of the imminium ion. The whole
  • ][39][40][41][42][43]. We have recently reported a post-Ugi gold-catalyzed intramolecular domino cyclization sequence which produces spiroindolines (Scheme 1) [44]. The first step in this sequence is an Ugi four-component reaction (Ugi-4CR) [4][5] with 2-alkynoic acid as an alkyne source. The second
  • step is a cationic gold-catalyzed intramolecular hydroarylation tandem cyclization to produce spiroindolines with complete diastereoselectivity. This synthetic sequence is atom economic and mild conditions are applied to generate a very complex molecular structure from readily available starting
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Published 14 Oct 2013

Total synthesis of (−)-epimyrtine by a gold-catalyzed hydroamination approach

  • Thi Thanh Huyen Trinh,
  • Khanh Hung Nguyen,
  • Patricia de Aguiar Amaral and
  • Nicolas Gouault

Beilstein J. Org. Chem. 2013, 9, 2042–2047, doi:10.3762/bjoc.9.242

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Published 09 Oct 2013

Gold catalysis for organic synthesis II

  • F. Dean Toste

Beilstein J. Org. Chem. 2013, 9, 2040–2041, doi:10.3762/bjoc.9.241

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  • applications to the synthesis of complex natural products. The field has also witnessed growth through the discovery of other modes of reactivity. For example, gold-catalyzed cycloaddition reactions, examples of which are found in this Thematic Series, have featured prominently. Additionally, enantioselective
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Published 09 Oct 2013

Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes

  • Marcia E. Richard,
  • Daniel V. Fraccica,
  • Kevin J. Garcia,
  • Erica J. Miller,
  • Rosa M. Ciccarelli,
  • Erin C. Holahan,
  • Victoria L. Resh,
  • Aakash Shah,
  • Peter M. Findeis and
  • Robert A. Stockland Jr.

Beilstein J. Org. Chem. 2013, 9, 2002–2008, doi:10.3762/bjoc.9.235

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  • is focused on the elimination of solvents and additives from the synthetic methodology [10]. Thus, the design of gold catalyzed reactions that proceed under solvent-free conditions and without the addition of silver salts or acidic promoters would be of interest to those charged with designing
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Published 02 Oct 2013

Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives

  • Yin-wei Sun,
  • Qin Xu and
  • Min Shi

Beilstein J. Org. Chem. 2013, 9, 1969–1976, doi:10.3762/bjoc.9.233

Graphical Abstract
  • ]. It is well known that gold catalysts have different catalytic abilities compared with other transition metals [24]. Moreover, gold-catalyzed chemical transformations have made significant progress during the last 5 years [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44
  • interest in gold-catalyzed C–C [57][58][59][60][61] or C–X bond [62][63][64][65][66][67] formation reactions. So far, we have reported a variety of gold-catalyzed intramolecular rearrangements with highly strained small rings for C–C or C–X bond formations [57][58][59][62][63][64][65][66][67][68]. Based on
  • derivatives in the gold catalyzed intermolecular reaction of oxabicyclic alkenes with electron-deficient terminal alkynes under mild conditions [69][70][71][72][73][74][75][76] (Scheme 1). Results and Discussion To generate a new C–O bond in the reaction of oxabicyclic alkene 1a with electron-deficient
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Published 01 Oct 2013

An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine

  • Jörg Erdsack and
  • Norbert Krause

Beilstein J. Org. Chem. 2013, 9, 1936–1942, doi:10.3762/bjoc.9.229

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  • Jorg Erdsack Norbert Krause Organic Chemistry, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany 10.3762/bjoc.9.229 Abstract The synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine (22, normethylazafuranomycin) by the gold-catalyzed cycloisomerization of α
  • , removal of the double bond, or change of the relative configuration [14][16]. Likewise, carbafuranomycin (1b) showed insufficient biological activity [17]. In 2007, we reported a synthesis of furanomycin derivatives by gold-catalyzed endo-selective cycloisomerization of α-hydroxyallenes [19]. This method
  • ; then hydrazine monohydrate) [38][39][62]. Unfortunately, fluoride-mediated desilylation of allene 6c caused complete epimerization of the allenic chirality axis. Therefore, the silylallene was not used in further studies. The results of the gold-catalyzed cycloisomerization of the allenes 7 and 8 to
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Published 25 Sep 2013

Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes

  • Kegong Ji,
  • Jonathan Nelson and
  • Liming Zhang

Beilstein J. Org. Chem. 2013, 9, 1925–1930, doi:10.3762/bjoc.9.227

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  • Kegong Ji Jonathan Nelson Liming Zhang Department of Chemistry and Biochemistry, University of California, Santa Barbara, California, 93106, USA 10.3762/bjoc.9.227 Abstract Gold-catalyzed intermolecular oxidation of carboxylates of primary or secondary propargylic alcohols are realized with
  • carboxylate; Introduction We reported in 2010 [1] that α-oxo gold carbenes could be conveniently generated as reactive intermediates in gold-catalyzed intermolecular oxidation of alkynes. By using pyridine N-oxides [1] and later 8-substituted quinoline N-oxides [2] as the external oxidants, this approach
  • the sulfoxide, 5a-OAc was formed in only 5% yield even at 60 °C after 12 h (Scheme 4); moreover, the major product in the reaction was the expected enone 6 (56% yield, 88% conversion) due to a dominant gold-catalyzed 3,3-rearrangement; c) this alternative could not rationalize the formation of 5a-H
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Published 24 Sep 2013

Gold(I)-catalyzed formation of furans from γ-acyloxyalkynyl ketones

  • Marie Hoffmann,
  • Solène Miaskiewicz,
  • Jean-Marc Weibel,
  • Patrick Pale and
  • Aurélien Blanc

Beilstein J. Org. Chem. 2013, 9, 1774–1780, doi:10.3762/bjoc.9.206

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  • the nature of the migratory acyloxy group. We synthetized similar substrates 1e–1h bearing pivaloyl, benzoyl, acetyl and 2-phenylacetyl groups, respectively. These compounds were engaged in the gold-catalyzed process affording the furans 2e–2h in the same range of yields (70–80%), suggesting that the
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Published 30 Aug 2013

Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans

  • Yifan Li and
  • Jérôme Waser

Beilstein J. Org. Chem. 2013, 9, 1763–1767, doi:10.3762/bjoc.9.204

Graphical Abstract
  • knowledge, the direct alkynylation of benzofurans is still an unknown process. Since 2009, our group has developed a mild gold-catalyzed [14][15][16][17] method for the alkynylation of electron-rich aryls such as indoles and pyrroles [18], thiophenes [19], anilines [20] and furans [21]. Key for success was
  • silica gel and purified directly by column chromatography. Benzofurans in bioactive compounds and materials. Zinc–gold catalyzed C2-alkynylation of benzofurans. Scope of the reaction. Alkynylation of 7-methoxybenzofuran (7j) [31]. Alkynylation of 8-methoxypsoralen (2). Optimization of the alkynylation of
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Published 29 Aug 2013

Gold-catalyzed cyclization of allenyl acetal derivatives

  • Dhananjayan Vasu,
  • Samir Kundlik Pawar and
  • Rai-Shung Liu

Beilstein J. Org. Chem. 2013, 9, 1751–1756, doi:10.3762/bjoc.9.202

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  • Dhananjayan Vasu Samir Kundlik Pawar Rai-Shung Liu Department of Chemistry, National Tsing Hua University, Hsinchu, 30013, Taiwan (ROC) 10.3762/bjoc.9.202 Abstract The gold-catalyzed transformation of allenyl acetals into 5-alkylidenecyclopent-2-en-1-ones is described. The outcome of our
  • of the acetate group at the allyl cation intermediate. Keywords: allenyl acetals; 5-alkylidenecyclopent-2-en-1-ones; cyclization; gold catalysis; Introduction Gold-catalyzed cyclization/cycloaddition reactions [1][2][3][4][5] are useful synthetic methods to construct complicated carbo- and
  • one-pot procedure. We previously reported gold-catalyzed reactions of allenyl acetals with suitable dipolarophiles such as 1,3-diones to chemoselectively produce the cycloaddition product 2 [17] (Scheme 1). Similar reactions with nitrones stereoselectively delivered distinct formal cycloadducts 3 [18
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Published 27 Aug 2013

Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements

  • Jungho Jun,
  • Hyu-Suk Yeom,
  • Jun-Hyun An and
  • Seunghoon Shin

Beilstein J. Org. Chem. 2013, 9, 1724–1729, doi:10.3762/bjoc.9.198

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  • Jungho Jun Hyu-Suk Yeom Jun-Hyun An Seunghoon Shin Department of Chemistry and Institute for Natural Sciences, Hanyang University, Seoul, 133-791, Korea 10.3762/bjoc.9.198 Abstract Gold-catalyzed intermolecular couplings of sulfonylacetylenes with allyl ethers are reported. A cooperative
  • rearrangement should occur through antara-facial selectivity due to the orbital symmetry. Conclusion Gold catalyzed intermolecular coupling of allyl ethers with sulfonylacetylene has been reported. The strong polarizing effect of the sulfonyl group induced an effective intermolecular tandem carboalkoxylation
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Published 22 Aug 2013

Gold-catalyzed intermolecular hydroamination of allenes with sulfonamides

  • Chen Zhang,
  • Shao-Qiao Zhang,
  • Hua-Jun Cai and
  • Dong-Mei Cui

Beilstein J. Org. Chem. 2013, 9, 1045–1050, doi:10.3762/bjoc.9.117

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  • 7). Single crystals of the compound 3n suitable for X-ray crystallographic analysis were also obtained (Figure 2). This showed that 3n is the E isomer, the sulfonamide being trans to the diphenylmethyl groups (Figure 2). The proposed mechanism of the gold-catalyzed hydroaamination of allenes is
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Published 29 May 2013

Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones

  • Benito Alcaide,
  • Pedro Almendros,
  • M. Teresa Quirós and
  • Israel Fernández

Beilstein J. Org. Chem. 2013, 9, 818–826, doi:10.3762/bjoc.9.93

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  • gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out. Keywords: allenes; computational chemistry; gold; gold catalysis; heterocycles; reaction
  • ][37][38][39][40][41]. The Boc protective group has been widely used in allene chemistry, being an inert and recommended partner in gold- and palladium-catalyzed aminocyclizations of allenes [42]. On the other hand, reports of gold-catalyzed cyclizations leading to heterocycles that contain more than
  • ][53][54][55], we decided to examine the gold-catalyzed cyclization of N-Boc-allenes with the aim of establishing a protocol for the synthesis of 1,3-oxazin-2-one derivatives in which the carbamate group should serve as the source of CO2. Results and Discussion To explore the effects of various
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Published 26 Apr 2013

On the proposed structures and stereocontrolled synthesis of the cephalosporolides

  • Sami F. Tlais and
  • Gregory B. Dudley

Beilstein J. Org. Chem. 2012, 8, 1287–1292, doi:10.3762/bjoc.8.146

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  • internal alkyne 6, which was submitted to gold-catalyzed cycloisomerization [33] to afford spiroketals 7a and 7b (the silyl ether is concomitantly hydrolyzed) as a 1:1 mixture of isomers. Exposure of this mixture to zinc chloride promoted isomerization to provide 7a in >20:1 dr. TEMPO oxidation then
  • alkyne 5 with (S)-1,2 epoxynonane. Gold-catalyzed cycloisomerization (with desilylation) provided spiroketal diols 10a and 10b in a 32:68 ratio and in 89% total yield. Major spiroketal 10b could be converted to 10a in 15:1 dr by zinc-catalyzed isomerization. Both isomers (10a and 10b) were independently
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Published 14 Aug 2012

Synthesis of fluoranthenes by hydroarylation of alkynes catalyzed by gold(I) or gallium trichloride

  • Sergio Pascual,
  • Christophe Bour,
  • Paula de Mendoza and
  • Antonio M. Echavarren

Beilstein J. Org. Chem. 2011, 7, 1520–1525, doi:10.3762/bjoc.7.178

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  • the synthesis of complex molecules under mild conditions [1][2][3][4][5][6][7][8]. Alkynes can react in gold-catalyzed Friedel–Crafts-type reactions with arenes to give products resulting from the intermolecular hydroarylation of the alkynes (or alkenylation of the arenes) [9][10][11][12][13][14][15
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Published 14 Nov 2011

Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes

  • Elena Borsini,
  • Gianluigi Broggini,
  • Andrea Fasana,
  • Chiara Baldassarri,
  • Angelo M. Manzo and
  • Alcide D. Perboni

Beilstein J. Org. Chem. 2011, 7, 1468–1474, doi:10.3762/bjoc.7.170

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  • pyrrolo[2,3-c]pyridines (Scheme 1) [33]. The reaction provided also the isomeric pyrrolo[3,2-c]pyridines arising from 1,2-migration of the amide moiety. Having recently broadened our studies toward gold catalysis [34][35], we have been intrigued by the investigation of a gold-catalyzed intramolecular
  • considerations, the N-propargyl amides of 1H-pyrrole-2-carboxylic acids 1a,b, easily prepared in high yields from the corresponding 1H-pyrrole-2-carboxylic acids and N-methyl-N-propargylamine with DCC as coupling reagent, were submitted to gold-catalyzed reactions under different conditions (Table 1). First, it
  • of the seven-membered cyclized products could be due to a stabilizing effect of the phenyl group in the transition state of the reaction. Conclusion In summary, the cyclization of N-alkynyl pyrrole-2-carboxamides under very mild gold-catalyzed conditions has been described. The outcome of the
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Published 26 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

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  • the synthesis of 3-fluoro-2-methylene-pyrrolidine (3a) and -piperidine (3b) from 1,5- and 1,6-aminoalkynes, respectively, using a combination of a gold-catalyzed hydroamination reaction followed by electrophilic trapping of an intermediate cyclic enamine by Selectfluor. Careful attention was paid to
  • recently, in their study on the synthesis α-fluoro ketones, Nevado et al. observed the formation of fluorinated pyrrolidinol obtained by a gold-catalyzed cyclization of a 1,5-aminoalkyne in the presence of Selectfluor (Scheme 1) [3]. These authors proposed that the formation of the C(sp3)–F bond could be
  • hydrofluorination of alkynes catalyzed by N-heterocyclic carbene gold(I) complexes [4], or by fluorodeauration of transient vinyl gold species [5][6], has been previously reported in the literature. On the basis of our recent results on the gold-catalyzed cyclization of enynes [7][8][9][10] and allenylhydrazones
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Published 07 Oct 2011

Directed aromatic functionalization

  • Victor Snieckus

Beilstein J. Org. Chem. 2011, 7, 1215–1218, doi:10.3762/bjoc.7.141

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  • exception [32][33][34], to rationalize ortho selectivity. The aromatic ring annulative chemistry, which can be achieved by C–H-activation mediated processes, perhaps best exemplified by gold-catalyzed reactions [35][36], is astonishing and defies retrosynthetic analysis. While as yet mostly empirically
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Published 06 Sep 2011

Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols

  • Michel Chiarucci,
  • Mirko Locritani,
  • Gianpiero Cera and
  • Marco Bandini

Beilstein J. Org. Chem. 2011, 7, 1198–1204, doi:10.3762/bjoc.7.139

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  • to as π-activated alcohols), deserves a particular mention [10][11][12][13]. As a part of our ongoing interest in the gold-catalyzed allylic functionalization of C- and heteroatom-based nucleophiles with alcohols [14][15][16][17], we previously observed the formation of synthetically useful
  • reasonably rationalized in terms of the high π-acidity and poor oxophilicity of the Au(I) species [37]. With the optimal catalytic systems in hand (IMesAuOTf or [dppf(AuNTf2)2], DCE, 80 °C), we verified the generality of the method by subjecting a range of malonyl alcohols 1b–j to the gold-catalyzed
  • comparable yield (72%, entry 1) and similar diastereomeric ratio. Here, although the impact of the C─C double bond configuration on the stereochemical outcome of SN2′-type gold-catalyzed intramolecular O- [45] and N-alkylations [37][46] with allylic alcohols was demonstrated, we consider it likely that an
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Published 01 Sep 2011
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