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Rhodium-Catalyzed Regio- and Enantioselective Addition of N-Hydroxyphthalimide to Allenes: A Strategy To Synthesize Chiral Allylic Alcohols.

Organic letters

Liu Z, Breit B.
PMID: 29280635
Org Lett. 2018 Jan 05;20(1):300-303. doi: 10.1021/acs.orglett.7b03709. Epub 2017 Dec 27.

We achieved the first Rh-catalyzed regio- and enantioselective additions of N-hydroxyphthalimide to allenes. This transformation is accomplished via mild reaction conditions, leveraging on Josiphos SL-J003-2 as a chiral ligand to furnish branched O-allyl compounds in good yields with moderate...

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Liu Z, Breit B. Rhodium-Catalyzed Regio- and Enantioselective Addition of N-Hydroxyphthalimide to Allenes: A Strategy To Synthesize Chiral Allylic Alcohols. Org Lett. 2017;20(1):300-303doi: 10.1021/acs.orglett.7b03709.
Liu, Z., & Breit, B. (2018). Rhodium-Catalyzed Regio- and Enantioselective Addition of N-Hydroxyphthalimide to Allenes: A Strategy To Synthesize Chiral Allylic Alcohols. Organic letters, 20(1), 300-303. https://doi.org/10.1021/acs.orglett.7b03709
Liu, Zi, and Breit, Bernhard. "Rhodium-Catalyzed Regio- and Enantioselective Addition of N-Hydroxyphthalimide to Allenes: A Strategy To Synthesize Chiral Allylic Alcohols." Organic letters vol. 20,1 (2018): 300-303. doi: https://doi.org/10.1021/acs.orglett.7b03709
Liu Z, Breit B. Rhodium-Catalyzed Regio- and Enantioselective Addition of N-Hydroxyphthalimide to Allenes: A Strategy To Synthesize Chiral Allylic Alcohols. Org Lett. 2018 Jan 05;20(1):300-303. doi: 10.1021/acs.orglett.7b03709. Epub 2017 Dec 27. PMID: 29280635.
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Divergent access to N-hydroxypyrroles and isoxazoles via the gold(i)- or Brønsted acid-catalysed regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes.

Organic & biomolecular chemistry

Zeng Q, Zhang L, Xiao Y, Zhang J.
PMID: 29411001
Org Biomol Chem. 2018 Feb 21;16(8):1375-1380. doi: 10.1039/c7ob03107f.

The divergent regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes by a suitable choice of a gold(i) or a Brønsted acid catalyst, leading to 4-trifluoromethyl-N-hydroxypyrroles or 4-trifluoromethyl-5-alkylisoxazoles was developed. In order to avoid the tedious separation of unstable N-(2-trifluoromethyl-3-alkynyl) oximes, an easy...

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Zeng Q, Zhang L, Xiao Y, et al. Divergent access to N-hydroxypyrroles and isoxazoles via the gold(i)- or Brønsted acid-catalysed regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes. Org Biomol Chem. 2018;16(8):1375-1380doi: 10.1039/c7ob03107f.
Zeng, Q., Zhang, L., Xiao, Y., & Zhang, J. (2018). Divergent access to N-hydroxypyrroles and isoxazoles via the gold(i)- or Brønsted acid-catalysed regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes. Organic & biomolecular chemistry, 16(8), 1375-1380. https://doi.org/10.1039/c7ob03107f
Zeng, Qin, et al. "Divergent access to N-hydroxypyrroles and isoxazoles via the gold(i)- or Brønsted acid-catalysed regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes." Organic & biomolecular chemistry vol. 16,8 (2018): 1375-1380. doi: https://doi.org/10.1039/c7ob03107f
Zeng Q, Zhang L, Xiao Y, Zhang J. Divergent access to N-hydroxypyrroles and isoxazoles via the gold(i)- or Brønsted acid-catalysed regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes. Org Biomol Chem. 2018 Feb 21;16(8):1375-1380. doi: 10.1039/c7ob03107f. PMID: 29411001.
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Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines.

Organic letters

Dhanju S, Crich D.
PMID: 27053143
Org Lett. 2016 Apr 15;18(8):1820-3. doi: 10.1021/acs.orglett.6b00556. Epub 2016 Apr 07.

Diverse N,N,O-trisubstituted hydroxylamines, an under-represented group in compound collections, are readily prepared by partial reduction of N-acyloxy secondary amines with diisobutylaluminum hydride followed by acetylation and reduction of the so-formed O-acyl-N,N-disubstituted hydroxylamines with triethylsilane and boron trifluoride etherate. Use...

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Dhanju S, Crich D. Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines. Org Lett. 2016;18(8):1820-3doi: 10.1021/acs.orglett.6b00556.
Dhanju, S., & Crich, D. (2016). Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines. Organic letters, 18(8), 1820-3. https://doi.org/10.1021/acs.orglett.6b00556
Dhanju, Sandeep, and Crich, David. "Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines." Organic letters vol. 18,8 (2016): 1820-3. doi: https://doi.org/10.1021/acs.orglett.6b00556
Dhanju S, Crich D. Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines. Org Lett. 2016 Apr 15;18(8):1820-3. doi: 10.1021/acs.orglett.6b00556. Epub 2016 Apr 07. PMID: 27053143.
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Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds.

Journal of the American Chemical Society

Fan L, Hao J, Yu J, Ma X, Liu J, Luan X.
PMID: 32182059
J Am Chem Soc. 2020 Apr 08;142(14):6698-6707. doi: 10.1021/jacs.0c00403. Epub 2020 Mar 27.

Conventional approaches on using hydroxylamine derivatives as single nitrogen sources, for the construction of

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Fan L, Hao J, Yu J, et al. Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds. J Am Chem Soc. 2020;142(14):6698-6707doi: 10.1021/jacs.0c00403.
Fan, L., Hao, J., Yu, J., Ma, X., Liu, J., & Luan, X. (2020). Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds. Journal of the American Chemical Society, 142(14), 6698-6707. https://doi.org/10.1021/jacs.0c00403
Fan, Liangxin, et al. "Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds." Journal of the American Chemical Society vol. 142,14 (2020): 6698-6707. doi: https://doi.org/10.1021/jacs.0c00403
Fan L, Hao J, Yu J, Ma X, Liu J, Luan X. Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds. J Am Chem Soc. 2020 Apr 08;142(14):6698-6707. doi: 10.1021/jacs.0c00403. Epub 2020 Mar 27. PMID: 32182059.
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Mechanism-Based Design of Quinoline Potassium Acyltrifluoroborates for Rapid Amide-Forming Ligations at Physiological pH.

Journal of the American Chemical Society

Tanriver M, Dzeng YC, Da Ros S, Lam E, Bode JW.
PMID: 34647724
J Am Chem Soc. 2021 Oct 27;143(42):17557-17565. doi: 10.1021/jacs.1c07354. Epub 2021 Oct 14.

Potassium acyltrifluoroborates (KATs) undergo chemoselective amide-forming ligations with hydroxylamines. Under aqueous, acidic conditions these ligations can proceed rapidly, with rate constants of ∼20 M

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Tanriver M, Dzeng YC, Da Ros S, et al. Mechanism-Based Design of Quinoline Potassium Acyltrifluoroborates for Rapid Amide-Forming Ligations at Physiological pH. J Am Chem Soc. 2021;143(42):17557-17565doi: 10.1021/jacs.1c07354.
Tanriver, M., Dzeng, Y. C., Da Ros, S., Lam, E., & Bode, J. W. (2021). Mechanism-Based Design of Quinoline Potassium Acyltrifluoroborates for Rapid Amide-Forming Ligations at Physiological pH. Journal of the American Chemical Society, 143(42), 17557-17565. https://doi.org/10.1021/jacs.1c07354
Tanriver, Matthias, et al. "Mechanism-Based Design of Quinoline Potassium Acyltrifluoroborates for Rapid Amide-Forming Ligations at Physiological pH." Journal of the American Chemical Society vol. 143,42 (2021): 17557-17565. doi: https://doi.org/10.1021/jacs.1c07354
Tanriver M, Dzeng YC, Da Ros S, Lam E, Bode JW. Mechanism-Based Design of Quinoline Potassium Acyltrifluoroborates for Rapid Amide-Forming Ligations at Physiological pH. J Am Chem Soc. 2021 Oct 27;143(42):17557-17565. doi: 10.1021/jacs.1c07354. Epub 2021 Oct 14. PMID: 34647724.
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Kinetic resolution of indolines by asymmetric hydroxylamine formation.

Nature communications

Wang G, Lu R, He C, Liu L.
PMID: 33947847
Nat Commun. 2021 May 04;12(1):2512. doi: 10.1038/s41467-021-22658-3.

Catalytic kinetic resolution of amines represents a longstanding challenge in chemical synthesis. Here, we described a kinetic resolution of secondary amines through oxygenation to produce enantiopure hydroxylamines involving N-O bond formation. The economic and practical titanium-catalyzed asymmetric oxygenation with...

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Wang G, Lu R, He C, et al. Kinetic resolution of indolines by asymmetric hydroxylamine formation. Nat Commun. 2021;12(1):2512doi: 10.1038/s41467-021-22658-3.
Wang, G., Lu, R., He, C., & Liu, L. (2021). Kinetic resolution of indolines by asymmetric hydroxylamine formation. Nature communications, 12(1), 2512. https://doi.org/10.1038/s41467-021-22658-3
Wang, Gang, et al. "Kinetic resolution of indolines by asymmetric hydroxylamine formation." Nature communications vol. 12,1 (2021): 2512. doi: https://doi.org/10.1038/s41467-021-22658-3
Wang G, Lu R, He C, Liu L. Kinetic resolution of indolines by asymmetric hydroxylamine formation. Nat Commun. 2021 May 04;12(1):2512. doi: 10.1038/s41467-021-22658-3. PMID: 33947847; PMCID: PMC8096955.
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Iridium-Catalyzed Acid-Assisted Hydrogenation of Oximes to Hydroxylamines.

Angewandte Chemie (International ed. in English)

Mas-Roselló J, Cope CJ, Tan E, Pinson B, Robinson A, Smejkal T, Cramer N.
PMID: 33886142
Angew Chem Int Ed Engl. 2021 Jul 05;60(28):15524-15532. doi: 10.1002/anie.202103806. Epub 2021 Jun 07.

We found that cyclometalated cyclopentadienyl iridium(III) complexes are uniquely efficient catalysts in homogeneous hydrogenation of oximes to hydroxylamine products. A stable iridium C,N-chelation is crucial, with alkoxy-substituted aryl ketimine ligands providing the best catalytic performance. Several Ir-complexes were mapped...

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Mas-Roselló J, Cope CJ, Tan E, et al. Iridium-Catalyzed Acid-Assisted Hydrogenation of Oximes to Hydroxylamines. Angew Chem Int Ed Engl. 2021;60(28):15524-15532doi: 10.1002/anie.202103806.
Mas-Roselló, J., Cope, C. J., Tan, E., Pinson, B., Robinson, A., Smejkal, T., & Cramer, N. (2021). Iridium-Catalyzed Acid-Assisted Hydrogenation of Oximes to Hydroxylamines. Angewandte Chemie (International ed. in English), 60(28), 15524-15532. https://doi.org/10.1002/anie.202103806
Mas-Roselló, Josep, et al. "Iridium-Catalyzed Acid-Assisted Hydrogenation of Oximes to Hydroxylamines." Angewandte Chemie (International ed. in English) vol. 60,28 (2021): 15524-15532. doi: https://doi.org/10.1002/anie.202103806
Mas-Roselló J, Cope CJ, Tan E, Pinson B, Robinson A, Smejkal T, Cramer N. Iridium-Catalyzed Acid-Assisted Hydrogenation of Oximes to Hydroxylamines. Angew Chem Int Ed Engl. 2021 Jul 05;60(28):15524-15532. doi: 10.1002/anie.202103806. Epub 2021 Jun 07. PMID: 33886142.
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Catalytic Reduction of Oximes to Hydroxylamines: Current Methods, Challenges and Opportunities.

Chemistry (Weinheim an der Bergstrasse, Germany)

Mas-Roselló J, Cramer N.
PMID: 34817089
Chemistry. 2021 Nov 24;e202103683. doi: 10.1002/chem.202103683. Epub 2021 Nov 24.

Catalytic reduction of oximes represents a direct efficient approach to synthesize valuable hydroxylamine derivatives. However this transformation presents significant challenges: oximes are hard to reduce and, if reactive, reductive cleavage of the weak N-O bond often leads to primary...

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Mas-Roselló J, Cramer N. Catalytic Reduction of Oximes to Hydroxylamines: Current Methods, Challenges and Opportunities. Chemistry. 2021;e202103683doi: 10.1002/chem.202103683.
Mas-Roselló, J., & Cramer, N. (2021). Catalytic Reduction of Oximes to Hydroxylamines: Current Methods, Challenges and Opportunities. Chemistry (Weinheim an der Bergstrasse, Germany), e202103683. https://doi.org/10.1002/chem.202103683
Mas-Roselló, Josep, and Cramer, Nicolai. "Catalytic Reduction of Oximes to Hydroxylamines: Current Methods, Challenges and Opportunities." Chemistry (Weinheim an der Bergstrasse, Germany) vol. (2021): e202103683. doi: https://doi.org/10.1002/chem.202103683
Mas-Roselló J, Cramer N. Catalytic Reduction of Oximes to Hydroxylamines: Current Methods, Challenges and Opportunities. Chemistry. 2021 Nov 24;e202103683. doi: 10.1002/chem.202103683. Epub 2021 Nov 24. PMID: 34817089.
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Showing 169 to 176 of 176 entries