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Chemoselective synthesis of substituted imines, secondary amines, and beta-amino carbonyl compounds from nitroaromatics through cascade reactions on gold catalysts.

Chemistry (Weinheim an der Bergstrasse, Germany)

Santos LL, Serna P, Corma A.
PMID: 19609994
Chemistry. 2009 Aug 17;15(33):8196-203. doi: 10.1002/chem.200900884.

Substituted imines, alpha,beta-unsaturated imines, substituted secondary amines, and beta-amino carbonyl compounds have been synthesized by means of new cascade reactions with mono- or bifunctional gold-based solid catalysts under mild reaction conditions. The related synthetic route involves the hydrogenation of...

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Santos LL, Serna P, Corma A. Chemoselective synthesis of substituted imines, secondary amines, and beta-amino carbonyl compounds from nitroaromatics through cascade reactions on gold catalysts. Chemistry. 2009;15(33):8196-203doi: 10.1002/chem.200900884.
Santos, L. L., Serna, P., & Corma, A. (2009). Chemoselective synthesis of substituted imines, secondary amines, and beta-amino carbonyl compounds from nitroaromatics through cascade reactions on gold catalysts. Chemistry (Weinheim an der Bergstrasse, Germany), 15(33), 8196-203. https://doi.org/10.1002/chem.200900884
Santos, Laura L, et al. "Chemoselective synthesis of substituted imines, secondary amines, and beta-amino carbonyl compounds from nitroaromatics through cascade reactions on gold catalysts." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 15,33 (2009): 8196-203. doi: https://doi.org/10.1002/chem.200900884
Santos LL, Serna P, Corma A. Chemoselective synthesis of substituted imines, secondary amines, and beta-amino carbonyl compounds from nitroaromatics through cascade reactions on gold catalysts. Chemistry. 2009 Aug 17;15(33):8196-203. doi: 10.1002/chem.200900884. PMID: 19609994.
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The spectral stability of several sunscreening agents on stratum corneum sheets.

International journal of cosmetic science

Kammeyer A, Westerhof W, Bolhuis PA, Ris AJ, Hische EA.
PMID: 19456975
Int J Cosmet Sci. 1987 Jun;9(3):125-36. doi: 10.1111/j.1467-2494.1987.tb00469.x.

Synopsis Film layers of seventeen commercially available sunscreen products and sixteen active ingredients on stratum corneum sheets were spectrophotometrically monitored before and after simulated solar irradiation. Fixed irradiation doses were given within the daily terrestrial limits. From the changes...

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Kammeyer A, Westerhof W, Bolhuis PA, et al. The spectral stability of several sunscreening agents on stratum corneum sheets. Int J Cosmet Sci. 1987;9(3):125-36doi: 10.1111/j.1467-2494.1987.tb00469.x.
Kammeyer, A., Westerhof, W., Bolhuis, P. A., Ris, A. J., & Hische, E. A. (1987). The spectral stability of several sunscreening agents on stratum corneum sheets. International journal of cosmetic science, 9(3), 125-36. https://doi.org/10.1111/j.1467-2494.1987.tb00469.x
Kammeyer, A, et al. "The spectral stability of several sunscreening agents on stratum corneum sheets." International journal of cosmetic science vol. 9,3 (1987): 125-36. doi: https://doi.org/10.1111/j.1467-2494.1987.tb00469.x
Kammeyer A, Westerhof W, Bolhuis PA, Ris AJ, Hische EA. The spectral stability of several sunscreening agents on stratum corneum sheets. Int J Cosmet Sci. 1987 Jun;9(3):125-36. doi: 10.1111/j.1467-2494.1987.tb00469.x. PMID: 19456975.
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Reactions of nitroxides 15. Cinnamates bearing a nitroxyl moiety synthesized using a Mizoroki-Heck cross-coupling reaction.

Beilstein journal of organic chemistry

Zakrzewski J, Huras B.
PMID: 26199672
Beilstein J Org Chem. 2015 Jul 13;11:1155-62. doi: 10.3762/bjoc.11.130. eCollection 2015.

Cinnamic acid derivatives bearing a nitroxyl moiety (2,2,6,6-tetramethyl-1-oxyl-4-piperidyl 3-E-aryl acrylates) were synthesized in 30-100% yield using a Mizoroki-Heck cross-coupling reaction between 4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl and iodobenzene derivatives in the presence of palladium(II) acetate coordinated with a tri(o-tolyl)phosphine ligand immobilized in a...

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Zakrzewski J, Huras B. Reactions of nitroxides 15. Cinnamates bearing a nitroxyl moiety synthesized using a Mizoroki-Heck cross-coupling reaction. Beilstein J Org Chem. 2015;11:1155-62doi: 10.3762/bjoc.11.130.
Zakrzewski, J., & Huras, B. (2015). Reactions of nitroxides 15. Cinnamates bearing a nitroxyl moiety synthesized using a Mizoroki-Heck cross-coupling reaction. Beilstein journal of organic chemistry, 111155-62. https://doi.org/10.3762/bjoc.11.130
Zakrzewski, Jerzy, and Huras, Bogumiła. "Reactions of nitroxides 15. Cinnamates bearing a nitroxyl moiety synthesized using a Mizoroki-Heck cross-coupling reaction." Beilstein journal of organic chemistry vol. 11 (2015): 1155-62. doi: https://doi.org/10.3762/bjoc.11.130
Zakrzewski J, Huras B. Reactions of nitroxides 15. Cinnamates bearing a nitroxyl moiety synthesized using a Mizoroki-Heck cross-coupling reaction. Beilstein J Org Chem. 2015 Jul 13;11:1155-62. doi: 10.3762/bjoc.11.130. eCollection 2015. PMID: 26199672; PMCID: PMC4505299.
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Differences of volatile constituents between unripe, partially ripe and ripe guayabita del pinar (Psidium salutare H.B.K.) fruit macerates.

Food chemistry

Pino JA, Queris O.
PMID: 26049984
Food Chem. 2008 Aug 15;109(4):722-6. doi: 10.1016/j.foodchem.2008.01.024. Epub 2008 Jan 21.

The effect of the maturation stages on the volatile constituents of the guayabita del pinar (Psidium salutare H.B.K.) fruit macerates was investigated during three different stages (unripe, partially ripe and ripe). Volatile compounds were isolated by continuous liquid-liquid extraction...

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Pino JA, Queris O. Differences of volatile constituents between unripe, partially ripe and ripe guayabita del pinar (Psidium salutare H.B.K.) fruit macerates. Food Chem. 2008;109(4):722-6doi: 10.1016/j.foodchem.2008.01.024.
Pino, J. A., & Queris, O. (2008). Differences of volatile constituents between unripe, partially ripe and ripe guayabita del pinar (Psidium salutare H.B.K.) fruit macerates. Food chemistry, 109(4), 722-6. https://doi.org/10.1016/j.foodchem.2008.01.024
Pino, Jorge A, and Queris, Oscar. "Differences of volatile constituents between unripe, partially ripe and ripe guayabita del pinar (Psidium salutare H.B.K.) fruit macerates." Food chemistry vol. 109,4 (2008): 722-6. doi: https://doi.org/10.1016/j.foodchem.2008.01.024
Pino JA, Queris O. Differences of volatile constituents between unripe, partially ripe and ripe guayabita del pinar (Psidium salutare H.B.K.) fruit macerates. Food Chem. 2008 Aug 15;109(4):722-6. doi: 10.1016/j.foodchem.2008.01.024. Epub 2008 Jan 21. PMID: 26049984.
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Reactivity of phenolic compounds towards free radicals under in vitro conditions.

Journal of food science and technology

Mathew S, Abraham TE, Zakaria ZA.
PMID: 26344993
J Food Sci Technol. 2015 Sep;52(9):5790-8. doi: 10.1007/s13197-014-1704-0. Epub 2015 Jan 08.

The free radical scavenging activity and reducing power of 16 phenolic compounds including four hydroxycinnamic acid derivatives namely ferulic acid, caffeic acid, sinapic acid and p-coumaric acid, benzoic acid and its derivatives namely protocatechuic acid, gallic acid and vanillic...

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Mathew S, Abraham TE, Zakaria ZA. Reactivity of phenolic compounds towards free radicals under in vitro conditions. J Food Sci Technol. 2015;52(9):5790-8doi: 10.1007/s13197-014-1704-0.
Mathew, S., Abraham, T. E., & Zakaria, Z. A. (2015). Reactivity of phenolic compounds towards free radicals under in vitro conditions. Journal of food science and technology, 52(9), 5790-8. https://doi.org/10.1007/s13197-014-1704-0
Mathew, Sindhu, et al. "Reactivity of phenolic compounds towards free radicals under in vitro conditions." Journal of food science and technology vol. 52,9 (2015): 5790-8. doi: https://doi.org/10.1007/s13197-014-1704-0
Mathew S, Abraham TE, Zakaria ZA. Reactivity of phenolic compounds towards free radicals under in vitro conditions. J Food Sci Technol. 2015 Sep;52(9):5790-8. doi: 10.1007/s13197-014-1704-0. Epub 2015 Jan 08. PMID: 26344993; PMCID: PMC4554629.
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The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters.

Angewandte Chemie (International ed. in English)

Gatzenmeier T, Kaib PSJ, Lingnau JB, Goddard R, List B.
PMID: 29232022
Angew Chem Int Ed Engl. 2018 Feb 23;57(9):2464-2468. doi: 10.1002/anie.201712088. Epub 2018 Jan 26.

α,β-Unsaturated esters are readily available but challenging substrates to activate in asymmetric catalysis. We now describe an efficient, general, and highly enantioselective Mukaiyama-Michael reaction of silyl ketene acetals with α,β-unsaturated methyl esters that is catalyzed by a silylium imidodiphosphorimidate...

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Gatzenmeier T, Kaib PSJ, Lingnau JB, et al. The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters. Angew Chem Int Ed Engl. 2018;57(9):2464-2468doi: 10.1002/anie.201712088.
Gatzenmeier, T., Kaib, P. S. J., Lingnau, J. B., Goddard, R., & List, B. (2018). The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters. Angewandte Chemie (International ed. in English), 57(9), 2464-2468. https://doi.org/10.1002/anie.201712088
Gatzenmeier, Tim, et al. "The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters." Angewandte Chemie (International ed. in English) vol. 57,9 (2018): 2464-2468. doi: https://doi.org/10.1002/anie.201712088
Gatzenmeier T, Kaib PSJ, Lingnau JB, Goddard R, List B. The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters. Angew Chem Int Ed Engl. 2018 Feb 23;57(9):2464-2468. doi: 10.1002/anie.201712088. Epub 2018 Jan 26. PMID: 29232022.
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Bromo- or Methoxy-Group-Promoted Umpolung Electron Transfer Enabled, Visible-Light-Mediated Synthesis of 2-Substituted Indole-3-glyoxylates.

Organic letters

Vidyasagar A, Shi J, Kreitmeier P, Reiser O.
PMID: 30398887
Org Lett. 2018 Nov 16;20(22):6984-6989. doi: 10.1021/acs.orglett.8b02725. Epub 2018 Nov 06.

A visible-light-mediated radical tandem cyclization of ortho-isocyano-α-bromo cinnamates to 2-substituted indole-3-glyoxylates is achieved by formation of both C-C/C-S and C-O bonds. The reaction proceeds through a hitherto unprecedented bromine- or methoxy-group-promoted umpolung back electron transfer from an α-carbonyl radical...

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Vidyasagar A, Shi J, Kreitmeier P, et al. Bromo- or Methoxy-Group-Promoted Umpolung Electron Transfer Enabled, Visible-Light-Mediated Synthesis of 2-Substituted Indole-3-glyoxylates. Org Lett. 2018;20(22):6984-6989doi: 10.1021/acs.orglett.8b02725.
Vidyasagar, A., Shi, J., Kreitmeier, P., & Reiser, O. (2018). Bromo- or Methoxy-Group-Promoted Umpolung Electron Transfer Enabled, Visible-Light-Mediated Synthesis of 2-Substituted Indole-3-glyoxylates. Organic letters, 20(22), 6984-6989. https://doi.org/10.1021/acs.orglett.8b02725
Vidyasagar, Adiyala, et al. "Bromo- or Methoxy-Group-Promoted Umpolung Electron Transfer Enabled, Visible-Light-Mediated Synthesis of 2-Substituted Indole-3-glyoxylates." Organic letters vol. 20,22 (2018): 6984-6989. doi: https://doi.org/10.1021/acs.orglett.8b02725
Vidyasagar A, Shi J, Kreitmeier P, Reiser O. Bromo- or Methoxy-Group-Promoted Umpolung Electron Transfer Enabled, Visible-Light-Mediated Synthesis of 2-Substituted Indole-3-glyoxylates. Org Lett. 2018 Nov 16;20(22):6984-6989. doi: 10.1021/acs.orglett.8b02725. Epub 2018 Nov 06. PMID: 30398887.
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Catalytic asymmetric (4 + 1) annulation of nitroalkenes with allylic acetates: stereoselective synthesis of isoxazoline N-oxides.

Organic & biomolecular chemistry

Luo J, Chen R, Fan X, Gong J, Han J, He Z.
PMID: 31298257
Org Biomol Chem. 2019 Jul 24;17(29):6989-6993. doi: 10.1039/c9ob01058k.

An asymmetric (4 + 1) annulation of α-nitro cinnamates with Morita-Baylis-Hillman (MBH) acetates catalyzed by α-isocupreine is reported. It provides chiral isoxazoline N-oxides in moderate to good yields with 88-99% ee, and represents the first catalytic asymmetric (4 +...

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Luo J, Chen R, Fan X, et al. Catalytic asymmetric (4 + 1) annulation of nitroalkenes with allylic acetates: stereoselective synthesis of isoxazoline N-oxides. Org Biomol Chem. 2019;17(29):6989-6993doi: 10.1039/c9ob01058k.
Luo, J., Chen, R., Fan, X., Gong, J., Han, J., & He, Z. (2019). Catalytic asymmetric (4 + 1) annulation of nitroalkenes with allylic acetates: stereoselective synthesis of isoxazoline N-oxides. Organic & biomolecular chemistry, 17(29), 6989-6993. https://doi.org/10.1039/c9ob01058k
Luo, Jinghua, et al. "Catalytic asymmetric (4 + 1) annulation of nitroalkenes with allylic acetates: stereoselective synthesis of isoxazoline N-oxides." Organic & biomolecular chemistry vol. 17,29 (2019): 6989-6993. doi: https://doi.org/10.1039/c9ob01058k
Luo J, Chen R, Fan X, Gong J, Han J, He Z. Catalytic asymmetric (4 + 1) annulation of nitroalkenes with allylic acetates: stereoselective synthesis of isoxazoline N-oxides. Org Biomol Chem. 2019 Jul 24;17(29):6989-6993. doi: 10.1039/c9ob01058k. PMID: 31298257.
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Supramolecular chirality transfer in a stereodynamic catalysts.

Chirality

Storch G, Trapp O.
PMID: 30103282
Chirality. 2018 Oct;30(10):1150-1160. doi: 10.1002/chir.23007. Epub 2018 Aug 13.

We present rhodium catalysts that contain stereodynamic axially chiral biphenol-derived phosphinite ligands modified with non-stereoselective amides for non-covalent interactions. A chirality transfer was achieved with (R)- or (S)-acetylphenylalanine methyl amide, and the interaction mechanism was investigated by NMR measurements....

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Storch G, Trapp O. Supramolecular chirality transfer in a stereodynamic catalysts. Chirality. 2018;30(10):1150-1160doi: 10.1002/chir.23007.
Storch, G., & Trapp, O. (2018). Supramolecular chirality transfer in a stereodynamic catalysts. Chirality, 30(10), 1150-1160. https://doi.org/10.1002/chir.23007
Storch, Golo, and Trapp, Oliver. "Supramolecular chirality transfer in a stereodynamic catalysts." Chirality vol. 30,10 (2018): 1150-1160. doi: https://doi.org/10.1002/chir.23007
Storch G, Trapp O. Supramolecular chirality transfer in a stereodynamic catalysts. Chirality. 2018 Oct;30(10):1150-1160. doi: 10.1002/chir.23007. Epub 2018 Aug 13. PMID: 30103282.
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Post-Polymerization Modification of Ring Opening Metathesis Polymerization (ROMP)-Derived Materials Using Wittig Reactions.

Polymers

Duty R, Hobbs C.
PMID: 32486087
Polymers (Basel). 2020 May 29;12(6). doi: 10.3390/polym12061247.

This communication describes our recent efforts to utilize Wittig olefination reactions for the post-polymerization modification of polynorbornene derivatives prepared through ring opening metathesis polymerization (ROMP). Polymerizing α-bromo ester-containing norbornenes provides polymers that can undergo facile substitution with triphenylphosphine. The...

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Duty R, Hobbs C. Post-Polymerization Modification of Ring Opening Metathesis Polymerization (ROMP)-Derived Materials Using Wittig Reactions. Polymers (Basel). 2020;12(6)doi: 10.3390/polym12061247.
Duty, R., & Hobbs, C. (2020). Post-Polymerization Modification of Ring Opening Metathesis Polymerization (ROMP)-Derived Materials Using Wittig Reactions. Polymers, 12(6), . https://doi.org/10.3390/polym12061247
Duty, Ryan, and Hobbs, Christopher. "Post-Polymerization Modification of Ring Opening Metathesis Polymerization (ROMP)-Derived Materials Using Wittig Reactions." Polymers vol. 12,6 (2020). doi: https://doi.org/10.3390/polym12061247
Duty R, Hobbs C. Post-Polymerization Modification of Ring Opening Metathesis Polymerization (ROMP)-Derived Materials Using Wittig Reactions. Polymers (Basel). 2020 May 29;12(6). doi: 10.3390/polym12061247. PMID: 32486087; PMCID: PMC7361962.
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Semiquantitative FMO Analysis of Substituent Effect on the Reaction of Permanganate Ion with Unsymmetrical Alkenes.

The Journal of organic chemistry

Ogino T, Watanabe T, Matsuura M, Watanabe C, Ozaki H.
PMID: 11672129
J Org Chem. 1998 Apr 17;63(8):2627-2633. doi: 10.1021/jo972163k.

The substituent effects on the reactions of permanganate ion with unsymmetrical alkenes are analyzed on the assumption of a concerted (3 + 2) cycloaddition model by using an equation obtained by approximation based on the FMO theory in which...

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Ogino T, Watanabe T, Matsuura M, et al. Semiquantitative FMO Analysis of Substituent Effect on the Reaction of Permanganate Ion with Unsymmetrical Alkenes. J Org Chem. 1998;63(8):2627-2633doi: 10.1021/jo972163k.
Ogino, T., Watanabe, T., Matsuura, M., Watanabe, C., & Ozaki, H. (1998). Semiquantitative FMO Analysis of Substituent Effect on the Reaction of Permanganate Ion with Unsymmetrical Alkenes. The Journal of organic chemistry, 63(8), 2627-2633. https://doi.org/10.1021/jo972163k
Ogino, Toshio, et al. "Semiquantitative FMO Analysis of Substituent Effect on the Reaction of Permanganate Ion with Unsymmetrical Alkenes." The Journal of organic chemistry vol. 63,8 (1998): 2627-2633. doi: https://doi.org/10.1021/jo972163k
Ogino T, Watanabe T, Matsuura M, Watanabe C, Ozaki H. Semiquantitative FMO Analysis of Substituent Effect on the Reaction of Permanganate Ion with Unsymmetrical Alkenes. J Org Chem. 1998 Apr 17;63(8):2627-2633. doi: 10.1021/jo972163k. PMID: 11672129.
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Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst.

Organic letters

Shiomi T, Nishiyama H.
PMID: 17385871
Org Lett. 2007 Apr 26;9(9):1651-4. doi: 10.1021/ol070251d. Epub 2007 Mar 27.

[reaction: see text] The conjugate reduction of cinnamates with hydrosilane and chiral Rh(Phebox-ip) catalyst in the presence of excess acetone is shown to provide the corresponding intermolecular reductive aldol product in extremely high enantioselectivity (up to 98%). Several cinnamates...

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Shiomi T, Nishiyama H. Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst. Org Lett. 2007;9(9):1651-4doi: 10.1021/ol070251d.
Shiomi, T., & Nishiyama, H. (2007). Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst. Organic letters, 9(9), 1651-4. https://doi.org/10.1021/ol070251d
Shiomi, Takushi, and Nishiyama, Hisao. "Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst." Organic letters vol. 9,9 (2007): 1651-4. doi: https://doi.org/10.1021/ol070251d
Shiomi T, Nishiyama H. Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst. Org Lett. 2007 Apr 26;9(9):1651-4. doi: 10.1021/ol070251d. Epub 2007 Mar 27. PMID: 17385871.
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