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N-Arylazetidines: Preparation through Anionic Ring Closure.

The Journal of organic chemistry

Quinodoz P, Drouillat B, Wright K, Marrot J, Couty F.
PMID: 26932242
J Org Chem. 2016 Apr 01;81(7):2899-910. doi: 10.1021/acs.joc.6b00169. Epub 2016 Mar 10.

We report herein an efficient synthesis of diversely substituted N-aryl-2-cyanoazetidines based on an anionic ring-closure reaction. These compounds can be prepared from β-amino alcohols in enantiomerically pure form through a three-step sequence involving (i) copper-catalyzed N-arylation, (ii) N-cyanomethylation of...

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Quinodoz P, Drouillat B, Wright K, et al. N-Arylazetidines: Preparation through Anionic Ring Closure. J Org Chem. 2016;81(7):2899-910doi: 10.1021/acs.joc.6b00169.
Quinodoz, P., Drouillat, B., Wright, K., Marrot, J., & Couty, F. (2016). N-Arylazetidines: Preparation through Anionic Ring Closure. The Journal of organic chemistry, 81(7), 2899-910. https://doi.org/10.1021/acs.joc.6b00169
Quinodoz, Pierre, et al. "N-Arylazetidines: Preparation through Anionic Ring Closure." The Journal of organic chemistry vol. 81,7 (2016): 2899-910. doi: https://doi.org/10.1021/acs.joc.6b00169
Quinodoz P, Drouillat B, Wright K, Marrot J, Couty F. N-Arylazetidines: Preparation through Anionic Ring Closure. J Org Chem. 2016 Apr 01;81(7):2899-910. doi: 10.1021/acs.joc.6b00169. Epub 2016 Mar 10. PMID: 26932242.
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Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones.

Organic letters

Zhang S, Li L, Hu Y, Li Y, Yang Y, Zha Z, Wang Z.
PMID: 26414655
Org Lett. 2015 Oct 16;17(20):5036-9. doi: 10.1021/acs.orglett.5b02514. Epub 2015 Sep 28.

A general organocatalytic asymmetric dehydrated Mannich reaction of fluoroalkyl hemiaminals with ketones is reported. In this Mannich reaction, previously less explored aryl ketones showed great reactivity. By virtue of this efficient method, a wide range of biologically active β-amino...

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Zhang S, Li L, Hu Y, et al. Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones. Org Lett. 2015;17(20):5036-9doi: 10.1021/acs.orglett.5b02514.
Zhang, S., Li, L., Hu, Y., Li, Y., Yang, Y., Zha, Z., & Wang, Z. (2015). Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones. Organic letters, 17(20), 5036-9. https://doi.org/10.1021/acs.orglett.5b02514
Zhang, Sheng, et al. "Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones." Organic letters vol. 17,20 (2015): 5036-9. doi: https://doi.org/10.1021/acs.orglett.5b02514
Zhang S, Li L, Hu Y, Li Y, Yang Y, Zha Z, Wang Z. Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones. Org Lett. 2015 Oct 16;17(20):5036-9. doi: 10.1021/acs.orglett.5b02514. Epub 2015 Sep 28. PMID: 26414655.
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Organic Zeolite Analogues Based on Multi-Component Liquid Crystals: Recognition and Transformation of Molecules within Constrained Environments.

Materials (Basel, Switzerland)

Ishida Y.
PMID: 28879985
Materials (Basel). 2011 Jan 11;4(1):183-205. doi: 10.3390/ma4010183.

In liquid crystals (LCs), molecules are confined in peculiar environments, where ordered alignment and certain mobility are realized at the same time. Considering these characteristics, the idea of "controlling molecular events within LC media" seems reasonable. As a suitable...

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Ishida Y. Organic Zeolite Analogues Based on Multi-Component Liquid Crystals: Recognition and Transformation of Molecules within Constrained Environments. Materials (Basel). 2011;4(1):183-205doi: 10.3390/ma4010183.
Ishida, Y. (2011). Organic Zeolite Analogues Based on Multi-Component Liquid Crystals: Recognition and Transformation of Molecules within Constrained Environments. Materials (Basel, Switzerland), 4(1), 183-205. https://doi.org/10.3390/ma4010183
Ishida, Yasuhiro. "Organic Zeolite Analogues Based on Multi-Component Liquid Crystals: Recognition and Transformation of Molecules within Constrained Environments." Materials (Basel, Switzerland) vol. 4,1 (2011): 183-205. doi: https://doi.org/10.3390/ma4010183
Ishida Y. Organic Zeolite Analogues Based on Multi-Component Liquid Crystals: Recognition and Transformation of Molecules within Constrained Environments. Materials (Basel). 2011 Jan 11;4(1):183-205. doi: 10.3390/ma4010183. PMID: 28879985; PMCID: PMC5448478.
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Fe-catalyzed synthesis of substituted N-aryl oxazolidines.

Organic & biomolecular chemistry

Murru S, Lott CS, McGough B, Bernard DM, Srivastava RS.
PMID: 27001918
Org Biomol Chem. 2016 Apr 12;14(15):3681-5. doi: 10.1039/c6ob00185h.

A novel iron-catalyzed synthesis of substituted N-aryl oxazolidines was developed via C-N bond formation and methylenation. The reaction of aryl hydroxylamines with allyl alcohols, in the presence of formaldehyde or its equivalents, afforded variety of oxazolidine heterocycles in very...

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Murru S, Lott CS, McGough B, et al. Fe-catalyzed synthesis of substituted N-aryl oxazolidines. Org Biomol Chem. 2016;14(15):3681-5doi: 10.1039/c6ob00185h.
Murru, S., Lott, C. S., McGough, B., Bernard, D. M., & Srivastava, R. S. (2016). Fe-catalyzed synthesis of substituted N-aryl oxazolidines. Organic & biomolecular chemistry, 14(15), 3681-5. https://doi.org/10.1039/c6ob00185h
Murru, Siva, et al. "Fe-catalyzed synthesis of substituted N-aryl oxazolidines." Organic & biomolecular chemistry vol. 14,15 (2016): 3681-5. doi: https://doi.org/10.1039/c6ob00185h
Murru S, Lott CS, McGough B, Bernard DM, Srivastava RS. Fe-catalyzed synthesis of substituted N-aryl oxazolidines. Org Biomol Chem. 2016 Apr 12;14(15):3681-5. doi: 10.1039/c6ob00185h. PMID: 27001918.
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Synthesis of 1,4-amino alcohols by Grignard reagent addition to THF and N-tosyliminobenzyliodinane.

Organic & biomolecular chemistry

Tejo C, See YF, Mathiew M, Chan PW.
PMID: 26626538
Org Biomol Chem. 2016 Jan 21;14(3):844-8. doi: 10.1039/c5ob02302e. Epub 2015 Dec 02.

The synthesis of 1,4-amino alcohols from THF treated with N-tosyliminobenzyliodinane (PhINTs) followed by a Grignard reagent under mild reaction conditions at room temperature is described herein. Various Grignard reagents were shown to be compatible, furnishing the corresponding 4-substituted-N-1,4-tosylamino alcohols...

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Tejo C, See YF, Mathiew M, et al. Synthesis of 1,4-amino alcohols by Grignard reagent addition to THF and N-tosyliminobenzyliodinane. Org Biomol Chem. 2015;14(3):844-8doi: 10.1039/c5ob02302e.
Tejo, C., See, Y. F., Mathiew, M., & Chan, P. W. (2016). Synthesis of 1,4-amino alcohols by Grignard reagent addition to THF and N-tosyliminobenzyliodinane. Organic & biomolecular chemistry, 14(3), 844-8. https://doi.org/10.1039/c5ob02302e
Tejo, Ciputra, et al. "Synthesis of 1,4-amino alcohols by Grignard reagent addition to THF and N-tosyliminobenzyliodinane." Organic & biomolecular chemistry vol. 14,3 (2016): 844-8. doi: https://doi.org/10.1039/c5ob02302e
Tejo C, See YF, Mathiew M, Chan PW. Synthesis of 1,4-amino alcohols by Grignard reagent addition to THF and N-tosyliminobenzyliodinane. Org Biomol Chem. 2016 Jan 21;14(3):844-8. doi: 10.1039/c5ob02302e. Epub 2015 Dec 02. PMID: 26626538.
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Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols.

Beilstein journal of organic chemistry

Rossi B, Pastori N, Prosperini S, Punta C.
PMID: 25670994
Beilstein J Org Chem. 2015 Jan 15;11:66-73. doi: 10.3762/bjoc.11.10. eCollection 2015.

Following an optimized multicomponent procedure, an aryl amine, a ketone, and a cyclic ether or an alcohol molecule are assembled in a one-pot synthesis by nucleophilic radical addition of ketyl radicals to ketimines generated in situ. The reaction occurs...

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Rossi B, Pastori N, Prosperini S, et al. Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols. Beilstein J Org Chem. 2015;11:66-73doi: 10.3762/bjoc.11.10.
Rossi, B., Pastori, N., Prosperini, S., & Punta, C. (2015). Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols. Beilstein journal of organic chemistry, 1166-73. https://doi.org/10.3762/bjoc.11.10
Rossi, Bianca, et al. "Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols." Beilstein journal of organic chemistry vol. 11 (2015): 66-73. doi: https://doi.org/10.3762/bjoc.11.10
Rossi B, Pastori N, Prosperini S, Punta C. Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols. Beilstein J Org Chem. 2015 Jan 15;11:66-73. doi: 10.3762/bjoc.11.10. eCollection 2015. PMID: 25670994; PMCID: PMC4311587.
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Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols .

Tetrahedron, asymmetry

Wang HY, Huang K, De Jesús M, Espinosa S, Piñero-Santiago LE, Barnes CL, Ortiz-Marciales M.
PMID: 26843787
Tetrahedron Asymmetry. 2016 Feb 15;27(2):91-100. doi: 10.1016/j.tetasy.2015.12.002.

A practical and convenient method for the efficient and regio- and stereoselective ring-opening of enantiopure monosubstituted epoxides by sodium azide under hydrolytic conditions is reported. The ring-opening of enantiopure styryl and pyridyl (

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Wang HY, Huang K, De Jesús M, et al. Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols . Tetrahedron Asymmetry. 2016;27(2):91-100doi: 10.1016/j.tetasy.2015.12.002.
Wang, H. Y., Huang, K., De Jesús, M., Espinosa, S., Piñero-Santiago, L. E., Barnes, C. L., & Ortiz-Marciales, M. (2016). Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols . Tetrahedron, asymmetry, 27(2), 91-100. https://doi.org/10.1016/j.tetasy.2015.12.002
Wang, Hai-Yang, et al. "Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols ." Tetrahedron, asymmetry vol. 27,2 (2016): 91-100. doi: https://doi.org/10.1016/j.tetasy.2015.12.002
Wang HY, Huang K, De Jesús M, Espinosa S, Piñero-Santiago LE, Barnes CL, Ortiz-Marciales M. Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols . Tetrahedron Asymmetry. 2016 Feb 15;27(2):91-100. doi: 10.1016/j.tetasy.2015.12.002. PMID: 26843787; PMCID: PMC4733893.
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Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration.

Organic letters

Sun DY, Han GY, Gong JX, Nay B, Li XW, Guo YW.
PMID: 28111958
Org Lett. 2017 Feb 03;19(3):714-717. doi: 10.1021/acs.orglett.6b03892. Epub 2017 Jan 23.

The first total synthesis of a marine derived polyacetylene, distaminolyne A, and its enantiomer were achieved from the commercially available undec-10-en-1-ol. A key proline-catalyzed asymmetric α-aminooxylation of an aldehyde intermediate was used to introduce the chiral center en route...

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Sun DY, Han GY, Gong JX, et al. Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration. Org Lett. 2017;19(3):714-717doi: 10.1021/acs.orglett.6b03892.
Sun, D. Y., Han, G. Y., Gong, J. X., Nay, B., Li, X. W., & Guo, Y. W. (2017). Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration. Organic letters, 19(3), 714-717. https://doi.org/10.1021/acs.orglett.6b03892
Sun, Dong-Yu, et al. "Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration." Organic letters vol. 19,3 (2017): 714-717. doi: https://doi.org/10.1021/acs.orglett.6b03892
Sun DY, Han GY, Gong JX, Nay B, Li XW, Guo YW. Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration. Org Lett. 2017 Feb 03;19(3):714-717. doi: 10.1021/acs.orglett.6b03892. Epub 2017 Jan 23. PMID: 28111958.
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Catalytic Asymmetric Synthesis of N-Chiral Amine Oxides.

Angewandte Chemie (International ed. in English)

Bhadra S, Yamamoto H.
PMID: 27653750
Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13043-13046. doi: 10.1002/anie.201606354.

Direct asymmetric synthesis of N-chiral amine oxides was accomplished (up to 91:9 e.r.) by means of a bimetallic titanium catalyst. A hydroxy group situated at the γ-position of the N stereocenter enables the desired N-oxidation through dynamic kinetic resolution...

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Bhadra S, Yamamoto H. Catalytic Asymmetric Synthesis of N-Chiral Amine Oxides. Angew Chem Int Ed Engl. 2016;55(42):13043-13046doi: 10.1002/anie.201606354.
Bhadra, S., & Yamamoto, H. (2016). Catalytic Asymmetric Synthesis of N-Chiral Amine Oxides. Angewandte Chemie (International ed. in English), 55(42), 13043-13046. https://doi.org/10.1002/anie.201606354
Bhadra, Sukalyan, and Yamamoto, Hisashi. "Catalytic Asymmetric Synthesis of N-Chiral Amine Oxides." Angewandte Chemie (International ed. in English) vol. 55,42 (2016): 13043-13046. doi: https://doi.org/10.1002/anie.201606354
Bhadra S, Yamamoto H. Catalytic Asymmetric Synthesis of N-Chiral Amine Oxides. Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13043-13046. doi: 10.1002/anie.201606354. PMID: 27653750.
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Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications.

Beilstein journal of organic chemistry

Kristensen TE.
PMID: 25977719
Beilstein J Org Chem. 2015 Apr 08;11:446-68. doi: 10.3762/bjoc.11.51. eCollection 2015.

Amino acids, whether natural, semisynthetic or synthetic, are among the most important and useful chiral building blocks available for organic chemical synthesis. In principle, they can function as inexpensive, chiral and densely functionalized starting materials. On the other hand,...

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Kristensen TE. Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications. Beilstein J Org Chem. 2015;11:446-68doi: 10.3762/bjoc.11.51.
Kristensen, T. E. (2015). Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications. Beilstein journal of organic chemistry, 11446-68. https://doi.org/10.3762/bjoc.11.51
Kristensen, Tor E. "Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications." Beilstein journal of organic chemistry vol. 11 (2015): 446-68. doi: https://doi.org/10.3762/bjoc.11.51
Kristensen TE. Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications. Beilstein J Org Chem. 2015 Apr 08;11:446-68. doi: 10.3762/bjoc.11.51. eCollection 2015. PMID: 25977719; PMCID: PMC4419533.
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Approach to Monobactams and Nocardicins via Diastereoselective Kinugasa Reaction.

The Journal of organic chemistry

Kabala K, Grzeszczyk B, Stecko S, Furman B, Chmielewski M.
PMID: 26595720
J Org Chem. 2015 Dec 18;80(24):12038-46. doi: 10.1021/acs.joc.5b01979. Epub 2015 Dec 10.

A Kinugasa reaction between copper(I) acetylides and cyclic nitrones derived from chiral amino alcohols and glyoxylic acid is reported. The stereochemical preferences observed in this reaction are discussed. The alkyne molecule approaches the nitrone exclusively anti to the large...

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Kabala K, Grzeszczyk B, Stecko S, et al. Approach to Monobactams and Nocardicins via Diastereoselective Kinugasa Reaction. J Org Chem. 2015;80(24):12038-46doi: 10.1021/acs.joc.5b01979.
Kabala, K., Grzeszczyk, B., Stecko, S., Furman, B., & Chmielewski, M. (2015). Approach to Monobactams and Nocardicins via Diastereoselective Kinugasa Reaction. The Journal of organic chemistry, 80(24), 12038-46. https://doi.org/10.1021/acs.joc.5b01979
Kabala, Kamil, et al. "Approach to Monobactams and Nocardicins via Diastereoselective Kinugasa Reaction." The Journal of organic chemistry vol. 80,24 (2015): 12038-46. doi: https://doi.org/10.1021/acs.joc.5b01979
Kabala K, Grzeszczyk B, Stecko S, Furman B, Chmielewski M. Approach to Monobactams and Nocardicins via Diastereoselective Kinugasa Reaction. J Org Chem. 2015 Dec 18;80(24):12038-46. doi: 10.1021/acs.joc.5b01979. Epub 2015 Dec 10. PMID: 26595720.
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Remote chirality control based on the organocatalytic asymmetric Mannich reaction of α-thio acetaldehydes.

Chemical communications (Cambridge, England)

Kano T, Sakamoto R, Maruoka K.
PMID: 24305743
Chem Commun (Camb). 2014 Jan 28;50(8):942-4. doi: 10.1039/c3cc47827k.

Remote chirality control leading to 1,4-difunctionalized compounds such as 1,4-amino alcohols and 1,4-diamines was achieved by both syn- and anti-selective asymmetric Mannich reactions of α-thio acetaldehydes, the subsequent olefination and the stereospecific 2,3-sigmatropic rearrangement.

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Kano T, Sakamoto R, Maruoka K. Remote chirality control based on the organocatalytic asymmetric Mannich reaction of α-thio acetaldehydes. Chem Commun (Camb). 2014;50(8):942-4doi: 10.1039/c3cc47827k.
Kano, T., Sakamoto, R., & Maruoka, K. (2014). Remote chirality control based on the organocatalytic asymmetric Mannich reaction of α-thio acetaldehydes. Chemical communications (Cambridge, England), 50(8), 942-4. https://doi.org/10.1039/c3cc47827k
Kano, Taichi, et al. "Remote chirality control based on the organocatalytic asymmetric Mannich reaction of α-thio acetaldehydes." Chemical communications (Cambridge, England) vol. 50,8 (2014): 942-4. doi: https://doi.org/10.1039/c3cc47827k
Kano T, Sakamoto R, Maruoka K. Remote chirality control based on the organocatalytic asymmetric Mannich reaction of α-thio acetaldehydes. Chem Commun (Camb). 2014 Jan 28;50(8):942-4. doi: 10.1039/c3cc47827k. PMID: 24305743.
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