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Palladium-catalyzed asymmetric amination and imidation of 2,3-allenyl phosphates.

Organic letters

Imada Y, Nishida M, Kutsuwa K, Murahashi S, Naota T.
PMID: 16354079
Org Lett. 2005 Dec 22;7(26):5837-9. doi: 10.1021/ol0523502.

[reaction: see text] Asymmetric amination of 2,3-allenyl phosphates with nitrogen nucleophiles such as amines, hydroxylamines, and imides can be performed efficiently using a combination of zerovalent palladium complexes and SEGPHOS or MeOBIPHEP ligand, affording the corresponding optically active 1-aminated...

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Imada Y, Nishida M, Kutsuwa K, et al. Palladium-catalyzed asymmetric amination and imidation of 2,3-allenyl phosphates. Org Lett. 2005;7(26):5837-9doi: 10.1021/ol0523502.
Imada, Y., Nishida, M., Kutsuwa, K., Murahashi, S., & Naota, T. (2005). Palladium-catalyzed asymmetric amination and imidation of 2,3-allenyl phosphates. Organic letters, 7(26), 5837-9. https://doi.org/10.1021/ol0523502
Imada, Yasushi, et al. "Palladium-catalyzed asymmetric amination and imidation of 2,3-allenyl phosphates." Organic letters vol. 7,26 (2005): 5837-9. doi: https://doi.org/10.1021/ol0523502
Imada Y, Nishida M, Kutsuwa K, Murahashi S, Naota T. Palladium-catalyzed asymmetric amination and imidation of 2,3-allenyl phosphates. Org Lett. 2005 Dec 22;7(26):5837-9. doi: 10.1021/ol0523502. PMID: 16354079.
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Simple reaction conditions for the formation of ketonitrones from ketones and hydroxylamines.

The Journal of organic chemistry

Pfeiffer JY, Beauchemin AM.
PMID: 19791735
J Org Chem. 2009 Nov 06;74(21):8381-3. doi: 10.1021/jo901653d.

The condensation of ketones and hydroxylamines to form ketonitrones was reinvestigated by using thermal conditions previously found to minimize hydroxylamine decomposition (t-BuOH, 110 degrees C). This simple approach allows the formation of exocyclic, acyclic, and alpha,beta-unsaturated ketonitrones with benzylic,...

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Pfeiffer JY, Beauchemin AM. Simple reaction conditions for the formation of ketonitrones from ketones and hydroxylamines. J Org Chem. 2009;74(21):8381-3doi: 10.1021/jo901653d.
Pfeiffer, J. Y., & Beauchemin, A. M. (2009). Simple reaction conditions for the formation of ketonitrones from ketones and hydroxylamines. The Journal of organic chemistry, 74(21), 8381-3. https://doi.org/10.1021/jo901653d
Pfeiffer, Jennifer Y, and Beauchemin, André M. "Simple reaction conditions for the formation of ketonitrones from ketones and hydroxylamines." The Journal of organic chemistry vol. 74,21 (2009): 8381-3. doi: https://doi.org/10.1021/jo901653d
Pfeiffer JY, Beauchemin AM. Simple reaction conditions for the formation of ketonitrones from ketones and hydroxylamines. J Org Chem. 2009 Nov 06;74(21):8381-3. doi: 10.1021/jo901653d. PMID: 19791735.
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Oxidation of hydroxylamines to NO by plant cells.

Plant signaling & behavior

Rümer S, Kapuganti JG, Kaiser WM.
PMID: 19847118
Plant Signal Behav. 2009 Sep;4(9):853-5. doi: 10.4161/psb.4.9.9378. Epub 2009 Sep 22.

At least theoretically, plants may synthesize nitric oxide (NO) either by reduction of N in higher oxidations states, or by oxidation of more reduced N-compounds. The well established reductive pathway uses nitrite as a substrate, produced by cytosolic nitrate...

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Rümer S, Kapuganti JG, Kaiser WM. Oxidation of hydroxylamines to NO by plant cells. Plant Signal Behav. 2009;4(9):853-5doi: 10.4161/psb.4.9.9378.
Rümer, S., Kapuganti, J. G., & Kaiser, W. M. (2009). Oxidation of hydroxylamines to NO by plant cells. Plant signaling & behavior, 4(9), 853-5. https://doi.org/10.4161/psb.4.9.9378
Rümer, Stefan, et al. "Oxidation of hydroxylamines to NO by plant cells." Plant signaling & behavior vol. 4,9 (2009): 853-5. doi: https://doi.org/10.4161/psb.4.9.9378
Rümer S, Kapuganti JG, Kaiser WM. Oxidation of hydroxylamines to NO by plant cells. Plant Signal Behav. 2009 Sep;4(9):853-5. doi: 10.4161/psb.4.9.9378. Epub 2009 Sep 22. PMID: 19847118; PMCID: PMC2802794.
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Regio- and stereoselectivity in the decatungstate photocatalyzed alkylation of alkenes by alkylcyclohexanes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Dondi D, Ravelli D, Fagnoni M, Mella M, Molinari A, Maldotti A, Albini A.
PMID: 19609992
Chemistry. 2009 Aug 10;15(32):7949-57. doi: 10.1002/chem.200900810.

Tetrabutylammonium decatungstate (WO) photocatalyzes radical alkylation reactions starting directly from alkanes. When using tert-butylcyclohexane and methylcyclohexane as the radical precursors, the addition to electrophilic alkenes (beta,beta-dialkylmethylenemalononitriles, acrylonitrile, methyl acrylate, methyl vinyl ketone) is regioselective and exclusively gives 3- and...

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Dondi D, Ravelli D, Fagnoni M, et al. Regio- and stereoselectivity in the decatungstate photocatalyzed alkylation of alkenes by alkylcyclohexanes. Chemistry. 2009;15(32):7949-57doi: 10.1002/chem.200900810.
Dondi, D., Ravelli, D., Fagnoni, M., Mella, M., Molinari, A., Maldotti, A., & Albini, A. (2009). Regio- and stereoselectivity in the decatungstate photocatalyzed alkylation of alkenes by alkylcyclohexanes. Chemistry (Weinheim an der Bergstrasse, Germany), 15(32), 7949-57. https://doi.org/10.1002/chem.200900810
Dondi, Daniele, et al. "Regio- and stereoselectivity in the decatungstate photocatalyzed alkylation of alkenes by alkylcyclohexanes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 15,32 (2009): 7949-57. doi: https://doi.org/10.1002/chem.200900810
Dondi D, Ravelli D, Fagnoni M, Mella M, Molinari A, Maldotti A, Albini A. Regio- and stereoselectivity in the decatungstate photocatalyzed alkylation of alkenes by alkylcyclohexanes. Chemistry. 2009 Aug 10;15(32):7949-57. doi: 10.1002/chem.200900810. PMID: 19609992.
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Pharmacokinetics and metabolic fate of two nitroxides potentially useful as contrast agents for magnetic resonance imaging.

Pharmaceutical research

Couet WR, Eriksson UG, Tozer TN, Tuck LD, Wesbey GE, Nitecki D, Brasch RC.
PMID: 24277329
Pharm Res. 1984 Sep;1(5):203-9. doi: 10.1023/A:1016317212601.

Paramagnetic nitroxyl-containing compounds have been useful as contrast agents in magnetic resonance imaging (MRI) experiments in animals. Preliminary information on the metabolic fate, pharmacokinetic behavior, stability in tissues, and chemical reduction of two prototypic nitroxides, PCA and TES, is...

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Couet WR, Eriksson UG, Tozer TN, et al. Pharmacokinetics and metabolic fate of two nitroxides potentially useful as contrast agents for magnetic resonance imaging. Pharm Res. 1984;1(5):203-9doi: 10.1023/A:1016317212601.
Couet, W. R., Eriksson, U. G., Tozer, T. N., Tuck, L. D., Wesbey, G. E., Nitecki, D., & Brasch, R. C. (1984). Pharmacokinetics and metabolic fate of two nitroxides potentially useful as contrast agents for magnetic resonance imaging. Pharmaceutical research, 1(5), 203-9. https://doi.org/10.1023/A:1016317212601
Couet, W R, et al. "Pharmacokinetics and metabolic fate of two nitroxides potentially useful as contrast agents for magnetic resonance imaging." Pharmaceutical research vol. 1,5 (1984): 203-9. doi: https://doi.org/10.1023/A:1016317212601
Couet WR, Eriksson UG, Tozer TN, Tuck LD, Wesbey GE, Nitecki D, Brasch RC. Pharmacokinetics and metabolic fate of two nitroxides potentially useful as contrast agents for magnetic resonance imaging. Pharm Res. 1984 Sep;1(5):203-9. doi: 10.1023/A:1016317212601. PMID: 24277329.
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Synthesis, isomer count, and nuclear spin relaxation of H2O@open-C60 nitroxide derivatives.

Organic letters

Li Y, Lei X, Lawler RG, Murata Y, Komatsu K, Turro NJ.
PMID: 22804493
Org Lett. 2012 Aug 03;14(15):3822-5. doi: 10.1021/ol3013155. Epub 2012 Jul 17.

H(2)O@C(60) derivatives covalently linked to a nitroxide radical were synthesized. The (1)H NMR of the guest H(2)O revealed the formation of many isomers with broad signals. Reduction to the diamagnetic hydroxylamines sharpened the (1)H NMR signals considerably and allowed...

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Li Y, Lei X, Lawler RG, et al. Synthesis, isomer count, and nuclear spin relaxation of H2O@open-C60 nitroxide derivatives. Org Lett. 2012;14(15):3822-5doi: 10.1021/ol3013155.
Li, Y., Lei, X., Lawler, R. G., Murata, Y., Komatsu, K., & Turro, N. J. (2012). Synthesis, isomer count, and nuclear spin relaxation of H2O@open-C60 nitroxide derivatives. Organic letters, 14(15), 3822-5. https://doi.org/10.1021/ol3013155
Li, Yongjun, et al. "Synthesis, isomer count, and nuclear spin relaxation of H2O@open-C60 nitroxide derivatives." Organic letters vol. 14,15 (2012): 3822-5. doi: https://doi.org/10.1021/ol3013155
Li Y, Lei X, Lawler RG, Murata Y, Komatsu K, Turro NJ. Synthesis, isomer count, and nuclear spin relaxation of H2O@open-C60 nitroxide derivatives. Org Lett. 2012 Aug 03;14(15):3822-5. doi: 10.1021/ol3013155. Epub 2012 Jul 17. PMID: 22804493.
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Photoredox-Induced Radical Relay toward Functionalized β-Amino Alcohol Derivatives.

Organic letters

An XD, Jiao YY, Zhang H, Gao Y, Yu S.
PMID: 29314850
Org Lett. 2018 Jan 19;20(2):401-404. doi: 10.1021/acs.orglett.7b03693. Epub 2018 Jan 09.

A radical relay strategy is described to synthesize functionalized β-amino alcohols. This strategy is enabled by photoredox-catalyzed and nitrogen-centered radical-triggered cascade reactions of styrenes (or phenylacetylenes), enol derivatives, and O-acyl hydroxylamines in DMSO. The broad synthetic application of this...

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An XD, Jiao YY, Zhang H, et al. Photoredox-Induced Radical Relay toward Functionalized β-Amino Alcohol Derivatives. Org Lett. 2018;20(2):401-404doi: 10.1021/acs.orglett.7b03693.
An, X. D., Jiao, Y. Y., Zhang, H., Gao, Y., & Yu, S. (2018). Photoredox-Induced Radical Relay toward Functionalized β-Amino Alcohol Derivatives. Organic letters, 20(2), 401-404. https://doi.org/10.1021/acs.orglett.7b03693
An, Xiao-De, et al. "Photoredox-Induced Radical Relay toward Functionalized β-Amino Alcohol Derivatives." Organic letters vol. 20,2 (2018): 401-404. doi: https://doi.org/10.1021/acs.orglett.7b03693
An XD, Jiao YY, Zhang H, Gao Y, Yu S. Photoredox-Induced Radical Relay toward Functionalized β-Amino Alcohol Derivatives. Org Lett. 2018 Jan 19;20(2):401-404. doi: 10.1021/acs.orglett.7b03693. Epub 2018 Jan 09. PMID: 29314850.
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Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Kato K, Hirano K, Miura M.
PMID: 29512216
Chemistry. 2018 Apr 17;24(22):5775-5778. doi: 10.1002/chem.201801070. Epub 2018 Mar 23.

A CuCl/(R,R)-PTBP-BDPP-catalyzed regioselective and enantioselective aminoboration of simple and unactivated terminal alkenes with bis(pinacolato)diboron (pinB-Bpin) and hydroxylamines has been developed. The amino group and boryl group were incorporated at the internal position and terminal position, respectively, and the corresponding...

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Kato K, Hirano K, Miura M. Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes. Chemistry. 2018;24(22):5775-5778doi: 10.1002/chem.201801070.
Kato, K., Hirano, K., & Miura, M. (2018). Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes. Chemistry (Weinheim an der Bergstrasse, Germany), 24(22), 5775-5778. https://doi.org/10.1002/chem.201801070
Kato, Kodai, et al. "Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 24,22 (2018): 5775-5778. doi: https://doi.org/10.1002/chem.201801070
Kato K, Hirano K, Miura M. Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes. Chemistry. 2018 Apr 17;24(22):5775-5778. doi: 10.1002/chem.201801070. Epub 2018 Mar 23. PMID: 29512216.
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Hydroxylamine Derivatives as Nitrogen-Radical Precursors in Visible-Light Photochemistry.

Chemistry (Weinheim an der Bergstrasse, Germany)

Davies J, Morcillo SP, Douglas JJ, Leonori D.
PMID: 29787627
Chemistry. 2018 Aug 22;24(47):12154-12163. doi: 10.1002/chem.201801655. Epub 2018 Jul 06.

In recent years, hydroxylamines derivatives have been exploited as nitrogen-radical precursors in visible-light photochemistry. Their ability to serve as electrophores in redox chemistry has propelled the development of many novel transformations. Fundamental mechanistic aspects as well as the importance...

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Davies J, Morcillo SP, Douglas JJ, et al. Hydroxylamine Derivatives as Nitrogen-Radical Precursors in Visible-Light Photochemistry. Chemistry. 2018;24(47):12154-12163doi: 10.1002/chem.201801655.
Davies, J., Morcillo, S. P., Douglas, J. J., & Leonori, D. (2018). Hydroxylamine Derivatives as Nitrogen-Radical Precursors in Visible-Light Photochemistry. Chemistry (Weinheim an der Bergstrasse, Germany), 24(47), 12154-12163. https://doi.org/10.1002/chem.201801655
Davies, Jacob, et al. "Hydroxylamine Derivatives as Nitrogen-Radical Precursors in Visible-Light Photochemistry." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 24,47 (2018): 12154-12163. doi: https://doi.org/10.1002/chem.201801655
Davies J, Morcillo SP, Douglas JJ, Leonori D. Hydroxylamine Derivatives as Nitrogen-Radical Precursors in Visible-Light Photochemistry. Chemistry. 2018 Aug 22;24(47):12154-12163. doi: 10.1002/chem.201801655. Epub 2018 Jul 06. PMID: 29787627.
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Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow.

The Journal of organic chemistry

Audubert C, Bouchard A, Mathieu G, Lebel H.
PMID: 30354126
J Org Chem. 2018 Nov 16;83(22):14203-14209. doi: 10.1021/acs.joc.8b02387. Epub 2018 Nov 01.

The chemoselective amination of alkyl bromides and chlorides with aqueous ammonia and hydroxylamine was achieved in continuous flow to produce primary ammonium salts and hydroxylamines in high yields. An in-line workup was designed to isolate the corresponding primary amine,...

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Audubert C, Bouchard A, Mathieu G, et al. Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow. J Org Chem. 2018;83(22):14203-14209doi: 10.1021/acs.joc.8b02387.
Audubert, C., Bouchard, A., Mathieu, G., & Lebel, H. (2018). Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow. The Journal of organic chemistry, 83(22), 14203-14209. https://doi.org/10.1021/acs.joc.8b02387
Audubert, Clément, et al. "Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow." The Journal of organic chemistry vol. 83,22 (2018): 14203-14209. doi: https://doi.org/10.1021/acs.joc.8b02387
Audubert C, Bouchard A, Mathieu G, Lebel H. Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow. J Org Chem. 2018 Nov 16;83(22):14203-14209. doi: 10.1021/acs.joc.8b02387. Epub 2018 Nov 01. PMID: 30354126.
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Photocatalytic Reductive Fluoroalkylation of Nitrones.

Organic letters

Supranovich VI, Levin VV, Struchkova MI, Dilman AD.
PMID: 29355326
Org Lett. 2018 Feb 02;20(3):840-843. doi: 10.1021/acs.orglett.7b03987. Epub 2018 Jan 22.

A method for the addition of fluorinated groups to nitrones using an iridium photocatalyst and ascorbic acid as a stoichiometric reducing agent is described. The reaction proceeds through the generation of fluorinated radicals by single-electron reduction of fluorinated alkyl...

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Supranovich VI, Levin VV, Struchkova MI, et al. Photocatalytic Reductive Fluoroalkylation of Nitrones. Org Lett. 2018;20(3):840-843doi: 10.1021/acs.orglett.7b03987.
Supranovich, V. I., Levin, V. V., Struchkova, M. I., & Dilman, A. D. (2018). Photocatalytic Reductive Fluoroalkylation of Nitrones. Organic letters, 20(3), 840-843. https://doi.org/10.1021/acs.orglett.7b03987
Supranovich, Vyacheslav I, et al. "Photocatalytic Reductive Fluoroalkylation of Nitrones." Organic letters vol. 20,3 (2018): 840-843. doi: https://doi.org/10.1021/acs.orglett.7b03987
Supranovich VI, Levin VV, Struchkova MI, Dilman AD. Photocatalytic Reductive Fluoroalkylation of Nitrones. Org Lett. 2018 Feb 02;20(3):840-843. doi: 10.1021/acs.orglett.7b03987. Epub 2018 Jan 22. PMID: 29355326.
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From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines.

Organic letters

Das P, Almond DW, Tumbelty LN, Austin BE, Moura-Letts G.
PMID: 32602726
Org Lett. 2020 Jul 17;22(14):5491-5495. doi: 10.1021/acs.orglett.0c01846. Epub 2020 Jun 30.

Substituted and stereochemically dense carbacycles can be prepared by sequential dipolar cycloaddition and reductive cleavage from enals and hydroxylamines. The reaction sequence proceeds with high efficiency for a wide variety of enals and hydroxylamines. The reaction is regio- and...

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Das P, Almond DW, Tumbelty LN, et al. From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines. Org Lett. 2020;22(14):5491-5495doi: 10.1021/acs.orglett.0c01846.
Das, P., Almond, D. W., Tumbelty, L. N., Austin, B. E., & Moura-Letts, G. (2020). From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines. Organic letters, 22(14), 5491-5495. https://doi.org/10.1021/acs.orglett.0c01846
Das, Pulakesh, et al. "From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines." Organic letters vol. 22,14 (2020): 5491-5495. doi: https://doi.org/10.1021/acs.orglett.0c01846
Das P, Almond DW, Tumbelty LN, Austin BE, Moura-Letts G. From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines. Org Lett. 2020 Jul 17;22(14):5491-5495. doi: 10.1021/acs.orglett.0c01846. Epub 2020 Jun 30. PMID: 32602726.
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Showing 13 to 24 of 176 entries