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Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Langner M, Rémy P, Bolm C.
PMID: 16075444
Chemistry. 2005 Oct 21;11(21):6254-65. doi: 10.1002/chem.200500497.

The development of C1-symmetric aminosulfoximines, their highly modular synthesis, and their application in enantioselective copper-catalyzed Mukaiyama-type aldol reactions between pyruvates and enolsilanes is described. In this context, the influence of the ligand architecture as well as the optimization of...

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Langner M, Rémy P, Bolm C. Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions. Chemistry. 2005;11(21):6254-65doi: 10.1002/chem.200500497.
Langner, M., Rémy, P., & Bolm, C. (2005). Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions. Chemistry (Weinheim an der Bergstrasse, Germany), 11(21), 6254-65. https://doi.org/10.1002/chem.200500497
Langner, Martin, et al. "Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 11,21 (2005): 6254-65. doi: https://doi.org/10.1002/chem.200500497
Langner M, Rémy P, Bolm C. Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions. Chemistry. 2005 Oct 21;11(21):6254-65. doi: 10.1002/chem.200500497. PMID: 16075444.
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Acid-mediated electrocyclic domino transformations of 5,5-disubstituted 1-amino-1-azapenta-1,4-dien-3-ones into dihydrospiroindenepyrazole and dihydroindenodiazepine derivatives.

The Journal of organic chemistry

Ghavtadze N, Fröhlich R, Würthwein EU.
PMID: 19459598
J Org Chem. 2009 Jun 19;74(12):4584-91. doi: 10.1021/jo900270e.

Trifluoromethyl-substituted 1-amino-1-azapenta-1,4-dien-3-ones 4, which are accessible in good yield from pyruvates 1 in a three-step procedure, undergo a cascade reaction involving inter alia two electrocyclizations upon treatment with a large excess of trifluoromethanesulfonic acid to give novel dihydrospiroindenepyrazole 5a-o...

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Ghavtadze N, Fröhlich R, Würthwein EU. Acid-mediated electrocyclic domino transformations of 5,5-disubstituted 1-amino-1-azapenta-1,4-dien-3-ones into dihydrospiroindenepyrazole and dihydroindenodiazepine derivatives. J Org Chem. 2009;74(12):4584-91doi: 10.1021/jo900270e.
Ghavtadze, N., Fröhlich, R., & Würthwein, E. U. (2009). Acid-mediated electrocyclic domino transformations of 5,5-disubstituted 1-amino-1-azapenta-1,4-dien-3-ones into dihydrospiroindenepyrazole and dihydroindenodiazepine derivatives. The Journal of organic chemistry, 74(12), 4584-91. https://doi.org/10.1021/jo900270e
Ghavtadze, Nugzar, et al. "Acid-mediated electrocyclic domino transformations of 5,5-disubstituted 1-amino-1-azapenta-1,4-dien-3-ones into dihydrospiroindenepyrazole and dihydroindenodiazepine derivatives." The Journal of organic chemistry vol. 74,12 (2009): 4584-91. doi: https://doi.org/10.1021/jo900270e
Ghavtadze N, Fröhlich R, Würthwein EU. Acid-mediated electrocyclic domino transformations of 5,5-disubstituted 1-amino-1-azapenta-1,4-dien-3-ones into dihydrospiroindenepyrazole and dihydroindenodiazepine derivatives. J Org Chem. 2009 Jun 19;74(12):4584-91. doi: 10.1021/jo900270e. PMID: 19459598.
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Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc.

Beilstein journal of organic chemistry

Aikawa K, Yabuuchi K, Torii K, Mikami K.
PMID: 29623119
Beilstein J Org Chem. 2018 Mar 07;14:576-582. doi: 10.3762/bjoc.14.44. eCollection 2018.

The catalytic asymmetric methylation of fluoroalkylated pyruvates is shown with dimethylzinc as a methylating reagent in the presence of a copper catalyst bearing a chiral phosphine ligand. This is the first catalytic asymmetric methylation to synthesize various α-fluoroalkylated tertiary...

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Aikawa K, Yabuuchi K, Torii K, et al. Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc. Beilstein J Org Chem. 2018;14:576-582doi: 10.3762/bjoc.14.44.
Aikawa, K., Yabuuchi, K., Torii, K., & Mikami, K. (2018). Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc. Beilstein journal of organic chemistry, 14576-582. https://doi.org/10.3762/bjoc.14.44
Aikawa, Kohsuke, et al. "Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc." Beilstein journal of organic chemistry vol. 14 (2018): 576-582. doi: https://doi.org/10.3762/bjoc.14.44
Aikawa K, Yabuuchi K, Torii K, Mikami K. Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc. Beilstein J Org Chem. 2018 Mar 07;14:576-582. doi: 10.3762/bjoc.14.44. eCollection 2018. PMID: 29623119; PMCID: PMC5852614.
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OBO-Protected Pyruvates as Reagents for the Synthesis of Functionalized Heteroaromatic Compounds.

Organic letters

Alves Esteves CH, Koyioni M, Christensen KE, Smith PD, Donohoe TJ.
PMID: 29906124
Org Lett. 2018 Jul 06;20(13):4048-4051. doi: 10.1021/acs.orglett.8b01614. Epub 2018 Jun 15.

Pd-catalyzed α-arylation of methyl-OBO-ketone (OBO = 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl) gives rise to arylated OBO-protected pyruvates. By appropriate prefunctionalization of the aryl ring or by subsequent functionalization at the α-carbonyl position of the arylated OBO-ketones, useful diketo OBO-protected carboxylates can be generated....

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Alves Esteves CH, Koyioni M, Christensen KE, et al. OBO-Protected Pyruvates as Reagents for the Synthesis of Functionalized Heteroaromatic Compounds. Org Lett. 2018;20(13):4048-4051doi: 10.1021/acs.orglett.8b01614.
Alves Esteves, C. H., Koyioni, M., Christensen, K. E., Smith, P. D., & Donohoe, T. J. (2018). OBO-Protected Pyruvates as Reagents for the Synthesis of Functionalized Heteroaromatic Compounds. Organic letters, 20(13), 4048-4051. https://doi.org/10.1021/acs.orglett.8b01614
Alves Esteves, C Henrique, et al. "OBO-Protected Pyruvates as Reagents for the Synthesis of Functionalized Heteroaromatic Compounds." Organic letters vol. 20,13 (2018): 4048-4051. doi: https://doi.org/10.1021/acs.orglett.8b01614
Alves Esteves CH, Koyioni M, Christensen KE, Smith PD, Donohoe TJ. OBO-Protected Pyruvates as Reagents for the Synthesis of Functionalized Heteroaromatic Compounds. Org Lett. 2018 Jul 06;20(13):4048-4051. doi: 10.1021/acs.orglett.8b01614. Epub 2018 Jun 15. PMID: 29906124.
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Aspects of enantioselective heterogeneous catalysis: structure and reactivity of (S)-(-)-1-(1-naphthyl)ethylamine on Pt[111].

Journal of the American Chemical Society

Bonello JM, Williams FJ, Lambert RM.
PMID: 12603161
J Am Chem Soc. 2003 Mar 05;125(9):2723-9. doi: 10.1021/ja028436x.

The molecular orientation, spatial distribution, and thermal behavior of the powerful chiral catalyst modifier precursor (S)-naphthylethylamine adsorbed on Pt[111] have been studied by NEXAFS, XPS, STM, and temperature programmed reaction. At 300 K, both in the presence and in...

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Bonello JM, Williams FJ, Lambert RM. Aspects of enantioselective heterogeneous catalysis: structure and reactivity of (S)-(-)-1-(1-naphthyl)ethylamine on Pt[111]. J Am Chem Soc. 2003;125(9):2723-9doi: 10.1021/ja028436x.
Bonello, J. M., Williams, F. J., & Lambert, R. M. (2003). Aspects of enantioselective heterogeneous catalysis: structure and reactivity of (S)-(-)-1-(1-naphthyl)ethylamine on Pt[111]. Journal of the American Chemical Society, 125(9), 2723-9. https://doi.org/10.1021/ja028436x
Bonello, Jonathan M, et al. "Aspects of enantioselective heterogeneous catalysis: structure and reactivity of (S)-(-)-1-(1-naphthyl)ethylamine on Pt[111]." Journal of the American Chemical Society vol. 125,9 (2003): 2723-9. doi: https://doi.org/10.1021/ja028436x
Bonello JM, Williams FJ, Lambert RM. Aspects of enantioselective heterogeneous catalysis: structure and reactivity of (S)-(-)-1-(1-naphthyl)ethylamine on Pt[111]. J Am Chem Soc. 2003 Mar 05;125(9):2723-9. doi: 10.1021/ja028436x. PMID: 12603161.
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Structure of an alpha-Keto beta-Amido Acid, 3-(Phenylacetamido)pyruvic Acid, and Its Methyl Ester in the Solid State and in Organic and Aqueous Solvents.

The Journal of organic chemistry

Curley K, Pratt RF.
PMID: 11671778
J Org Chem. 1997 Jun 27;62(13):4479-4483. doi: 10.1021/jo970223g.

3-(Phenylacetamido)pyruvic acid and its methyl ester both exist in the enol form in the solid state and when dissolved in organic solvents. In aqueous solution, the pK(a)'s of the enol acid are 3.28 (CO(2)H) and 10.14 (enolic OH) and...

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Curley K, Pratt RF. Structure of an alpha-Keto beta-Amido Acid, 3-(Phenylacetamido)pyruvic Acid, and Its Methyl Ester in the Solid State and in Organic and Aqueous Solvents. J Org Chem. 1997;62(13):4479-4483doi: 10.1021/jo970223g.
Curley, K., & Pratt, R. F. (1997). Structure of an alpha-Keto beta-Amido Acid, 3-(Phenylacetamido)pyruvic Acid, and Its Methyl Ester in the Solid State and in Organic and Aqueous Solvents. The Journal of organic chemistry, 62(13), 4479-4483. https://doi.org/10.1021/jo970223g
Curley, Kieran, and Pratt, R. F.. "Structure of an alpha-Keto beta-Amido Acid, 3-(Phenylacetamido)pyruvic Acid, and Its Methyl Ester in the Solid State and in Organic and Aqueous Solvents." The Journal of organic chemistry vol. 62,13 (1997): 4479-4483. doi: https://doi.org/10.1021/jo970223g
Curley K, Pratt RF. Structure of an alpha-Keto beta-Amido Acid, 3-(Phenylacetamido)pyruvic Acid, and Its Methyl Ester in the Solid State and in Organic and Aqueous Solvents. J Org Chem. 1997 Jun 27;62(13):4479-4483. doi: 10.1021/jo970223g. PMID: 11671778.
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Asymmetric Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by a Dinuclear Zinc Catalyst.

The Journal of organic chemistry

Hua YZ, Chen JW, Yang H, Wang MC.
PMID: 29294293
J Org Chem. 2018 Feb 02;83(3):1160-1166. doi: 10.1021/acs.joc.7b02599. Epub 2018 Jan 16.

A bimetallic cooperative catalysis model has been reported for the asymmetric Friedel-Crafts (F-C) alkylation of indoles with trifluoromethyl pyruvates using Trost's intramolecular dinuclear zinc complex as the catalyst. This dinuclear zinc catalyst was prepared in situ by reacting the...

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Hua YZ, Chen JW, Yang H, et al. Asymmetric Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by a Dinuclear Zinc Catalyst. J Org Chem. 2018;83(3):1160-1166doi: 10.1021/acs.joc.7b02599.
Hua, Y. Z., Chen, J. W., Yang, H., & Wang, M. C. (2018). Asymmetric Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by a Dinuclear Zinc Catalyst. The Journal of organic chemistry, 83(3), 1160-1166. https://doi.org/10.1021/acs.joc.7b02599
Hua, Yuan-Zhao, et al. "Asymmetric Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by a Dinuclear Zinc Catalyst." The Journal of organic chemistry vol. 83,3 (2018): 1160-1166. doi: https://doi.org/10.1021/acs.joc.7b02599
Hua YZ, Chen JW, Yang H, Wang MC. Asymmetric Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by a Dinuclear Zinc Catalyst. J Org Chem. 2018 Feb 02;83(3):1160-1166. doi: 10.1021/acs.joc.7b02599. Epub 2018 Jan 16. PMID: 29294293.
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Direct catalytic asymmetric aldol reactions of pyruvates: scope and mechanism.

Organic & biomolecular chemistry

Gathergood N, Juhl K, Poulsen TB, Thordrup K, Jørgensen KA.
PMID: 15034632
Org Biomol Chem. 2004 Apr 07;2(7):1077-85. doi: 10.1039/b316092k. Epub 2004 Mar 09.

The direct aldol reaction of 2-ketoesters catalyzed by chiral bisoxazoline copper(II) complexes has been investigated. First the direct homo-aldol reaction of ethyl pyruvate is reported which proceeds to give diethyl 2-hydroxy-2-methyl-4-oxoglutarate. This was isolated as the more stable optically...

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Gathergood N, Juhl K, Poulsen TB, et al. Direct catalytic asymmetric aldol reactions of pyruvates: scope and mechanism. Org Biomol Chem. 2004;2(7):1077-85doi: 10.1039/b316092k.
Gathergood, N., Juhl, K., Poulsen, T. B., Thordrup, K., & Jørgensen, K. A. (2004). Direct catalytic asymmetric aldol reactions of pyruvates: scope and mechanism. Organic & biomolecular chemistry, 2(7), 1077-85. https://doi.org/10.1039/b316092k
Gathergood, Nicholas, et al. "Direct catalytic asymmetric aldol reactions of pyruvates: scope and mechanism." Organic & biomolecular chemistry vol. 2,7 (2004): 1077-85. doi: https://doi.org/10.1039/b316092k
Gathergood N, Juhl K, Poulsen TB, Thordrup K, Jørgensen KA. Direct catalytic asymmetric aldol reactions of pyruvates: scope and mechanism. Org Biomol Chem. 2004 Apr 07;2(7):1077-85. doi: 10.1039/b316092k. Epub 2004 Mar 09. PMID: 15034632.
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The Effect of Pyruvates, Aldehydes and Methylene Blue on the Fermentation of Glucose by Yeast Juice and Zymin in Presence of Phosphate.

The Biochemical journal

Harden A, Henley FR.
PMID: 16742920
Biochem J. 1920 Oct;14(5):642-53. doi: 10.1042/bj0140642.

No abstract available.

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Harden A, Henley FR. The Effect of Pyruvates, Aldehydes and Methylene Blue on the Fermentation of Glucose by Yeast Juice and Zymin in Presence of Phosphate. Biochem J. 1920;14(5):642-53doi: 10.1042/bj0140642.
Harden, A., & Henley, F. R. (1920). The Effect of Pyruvates, Aldehydes and Methylene Blue on the Fermentation of Glucose by Yeast Juice and Zymin in Presence of Phosphate. The Biochemical journal, 14(5), 642-53. https://doi.org/10.1042/bj0140642
Harden, A, and Henley, F R. "The Effect of Pyruvates, Aldehydes and Methylene Blue on the Fermentation of Glucose by Yeast Juice and Zymin in Presence of Phosphate." The Biochemical journal vol. 14,5 (1920): 642-53. doi: https://doi.org/10.1042/bj0140642
Harden A, Henley FR. The Effect of Pyruvates, Aldehydes and Methylene Blue on the Fermentation of Glucose by Yeast Juice and Zymin in Presence of Phosphate. Biochem J. 1920 Oct;14(5):642-53. doi: 10.1042/bj0140642. PMID: 16742920; PMCID: PMC1258928.
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Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis.

Organic letters

Alves Esteves CH, Hall CJJ, Smith PD, Donohoe TJ.
PMID: 28920691
Org Lett. 2017 Oct 06;19(19):5248-5251. doi: 10.1021/acs.orglett.7b02524. Epub 2017 Sep 18.

A protected pyruvate equivalent is described that allows arylation and arylation/alkylation reactions to be performed at the methyl group. Utilization of the OBO derivative of the pyruvate ester allowed the application of palladium catalyzed arylation reactions together with subsequent...

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Alves Esteves CH, Hall CJJ, Smith PD, et al. Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis. Org Lett. 2017;19(19):5248-5251doi: 10.1021/acs.orglett.7b02524.
Alves Esteves, C. H., Hall, C. J. J., Smith, P. D., & Donohoe, T. J. (2017). Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis. Organic letters, 19(19), 5248-5251. https://doi.org/10.1021/acs.orglett.7b02524
Alves Esteves, C Henrique, et al. "Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis." Organic letters vol. 19,19 (2017): 5248-5251. doi: https://doi.org/10.1021/acs.orglett.7b02524
Alves Esteves CH, Hall CJJ, Smith PD, Donohoe TJ. Pyruvate Enolate Arylation and Alkylation: OBO Ester Protected Pyruvates as Useful Reagents in Organic Synthesis. Org Lett. 2017 Oct 06;19(19):5248-5251. doi: 10.1021/acs.orglett.7b02524. Epub 2017 Sep 18. PMID: 28920691.
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Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A.

The Journal of organic chemistry

Amin PM, Su Z, Wang S.
PMID: 34652914
J Org Chem. 2021 Nov 05;86(21):15318-15325. doi: 10.1021/acs.joc.1c01890. Epub 2021 Oct 15.

Gold-catalyzed cycloisomerization of propargyl pyruvates has been developed as a key reaction to prepare maleic anhydride-type natural products. By combining with chemoselective epoxidation of the formed γ-alkylidenebutenolides and oxidative cleavage of epoxides, the first synthesis of tricladolide D and...

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Amin PM, Su Z, Wang S. Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A. J Org Chem. 2021;86(21):15318-15325doi: 10.1021/acs.joc.1c01890.
Amin, P. M., Su, Z., & Wang, S. (2021). Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A. The Journal of organic chemistry, 86(21), 15318-15325. https://doi.org/10.1021/acs.joc.1c01890
Amin, Pathan Mosim, et al. "Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A." The Journal of organic chemistry vol. 86,21 (2021): 15318-15325. doi: https://doi.org/10.1021/acs.joc.1c01890
Amin PM, Su Z, Wang S. Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A. J Org Chem. 2021 Nov 05;86(21):15318-15325. doi: 10.1021/acs.joc.1c01890. Epub 2021 Oct 15. PMID: 34652914.
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Adsorption states and modifier-substrate interactions on Pt(111) relevant to the enantioselective hydrogenation of alkyl pyruvates in the Orito reaction.

Journal of the American Chemical Society

Lavoie S, Laliberté MA, McBreen PH.
PMID: 14677961
J Am Chem Soc. 2003 Dec 24;125(51):15756-7. doi: 10.1021/ja036700w.

Reflectance FTIR spectroscopy (RAIRS) was used to study the chemisorption and intermolecular interactions of methyl pyruvate and (+/-)-1-(1-naphthyl)ethylamine (NEA) on Pt(111). NEA serves, in this study, as a tractable model of a chiral modifier in the asymmetric hydrogenation of...

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Lavoie S, Laliberté MA, McBreen PH. Adsorption states and modifier-substrate interactions on Pt(111) relevant to the enantioselective hydrogenation of alkyl pyruvates in the Orito reaction. J Am Chem Soc. 2003;125(51):15756-7doi: 10.1021/ja036700w.
Lavoie, S., Laliberté, M. A., & McBreen, P. H. (2003). Adsorption states and modifier-substrate interactions on Pt(111) relevant to the enantioselective hydrogenation of alkyl pyruvates in the Orito reaction. Journal of the American Chemical Society, 125(51), 15756-7. https://doi.org/10.1021/ja036700w
Lavoie, S, et al. "Adsorption states and modifier-substrate interactions on Pt(111) relevant to the enantioselective hydrogenation of alkyl pyruvates in the Orito reaction." Journal of the American Chemical Society vol. 125,51 (2003): 15756-7. doi: https://doi.org/10.1021/ja036700w
Lavoie S, Laliberté MA, McBreen PH. Adsorption states and modifier-substrate interactions on Pt(111) relevant to the enantioselective hydrogenation of alkyl pyruvates in the Orito reaction. J Am Chem Soc. 2003 Dec 24;125(51):15756-7. doi: 10.1021/ja036700w. PMID: 14677961.
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Showing 1 to 12 of 21 entries