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Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3 + 2] cycloaddition reaction.

Organic & biomolecular chemistry

Hu H, Yu S, Zhu L, Zhou L, Zhong W.
PMID: 26584209
Org Biomol Chem. 2016 Jan 14;14(2):752-760. doi: 10.1039/c5ob01958c.

A series of air-stable ferrocenylphosphines LB1-LB8 were designed and prepared in high yields. (R,SFc)-ferrocenylphosphine LB5 was found to efficiently promote the asymmetric [3 + 2] cycloaddition of Morita-Baylis-Hillman carbonates with maleimides to afford the corresponding bicyclic imides with 84-99%...

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Hu H, Yu S, Zhu L, et al. Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3 + 2] cycloaddition reaction. Org Biomol Chem. 2016;14(2):752-760doi: 10.1039/c5ob01958c.
Hu, H., Yu, S., Zhu, L., Zhou, L., & Zhong, W. (2016). Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3 + 2] cycloaddition reaction. Organic & biomolecular chemistry, 14(2), 752-760. https://doi.org/10.1039/c5ob01958c
Hu, Haiwen, et al. "Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3 + 2] cycloaddition reaction." Organic & biomolecular chemistry vol. 14,2 (2016): 752-760. doi: https://doi.org/10.1039/c5ob01958c
Hu H, Yu S, Zhu L, Zhou L, Zhong W. Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3 + 2] cycloaddition reaction. Org Biomol Chem. 2016 Jan 14;14(2):752-760. doi: 10.1039/c5ob01958c. PMID: 26584209.
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Copper-Mediated Oxidative Coupling of Benzamides with Maleimides via Directed C-H Cleavage.

Organic letters

Miura W, Hirano K, Miura M.
PMID: 26226391
Org Lett. 2015 Aug 21;17(16):4034-7. doi: 10.1021/acs.orglett.5b01940. Epub 2015 Jul 30.

A Cu(OAc)2/Cy2NMe-mediated oxidative direct coupling of benzamides with maleimides has been developed. The aromatic C-H alkenylation with the aid of an 8-aminoquinoline-based bidentate directing group is followed by an intramolecular aza-Michael-type addition to form the isoindolone-incorporated spirosuccinimides, which are...

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Miura W, Hirano K, Miura M. Copper-Mediated Oxidative Coupling of Benzamides with Maleimides via Directed C-H Cleavage. Org Lett. 2015;17(16):4034-7doi: 10.1021/acs.orglett.5b01940.
Miura, W., Hirano, K., & Miura, M. (2015). Copper-Mediated Oxidative Coupling of Benzamides with Maleimides via Directed C-H Cleavage. Organic letters, 17(16), 4034-7. https://doi.org/10.1021/acs.orglett.5b01940
Miura, Wataru, et al. "Copper-Mediated Oxidative Coupling of Benzamides with Maleimides via Directed C-H Cleavage." Organic letters vol. 17,16 (2015): 4034-7. doi: https://doi.org/10.1021/acs.orglett.5b01940
Miura W, Hirano K, Miura M. Copper-Mediated Oxidative Coupling of Benzamides with Maleimides via Directed C-H Cleavage. Org Lett. 2015 Aug 21;17(16):4034-7. doi: 10.1021/acs.orglett.5b01940. Epub 2015 Jul 30. PMID: 26226391.
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Chlorophyll-Catalyzed Visible-Light-Mediated Synthesis of Tetrahydroquinolines from N,N-Dimethylanilines and Maleimides.

The Journal of organic chemistry

Guo JT, Yang DC, Guan Z, He YH.
PMID: 28107007
J Org Chem. 2017 Feb 17;82(4):1888-1894. doi: 10.1021/acs.joc.6b03034. Epub 2017 Feb 05.

Natural pigment chlorophyll was used as a green photosensitizer for the first time in a visible-light photoredox catalysis for the efficient synthesis of tetrahydroquinolines from N,N-dimethylanilines and maleimides in an air atmosphere. The reaction involves direct cyclization via an...

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Guo JT, Yang DC, Guan Z, et al. Chlorophyll-Catalyzed Visible-Light-Mediated Synthesis of Tetrahydroquinolines from N,N-Dimethylanilines and Maleimides. J Org Chem. 2017;82(4):1888-1894doi: 10.1021/acs.joc.6b03034.
Guo, J. T., Yang, D. C., Guan, Z., & He, Y. H. (2017). Chlorophyll-Catalyzed Visible-Light-Mediated Synthesis of Tetrahydroquinolines from N,N-Dimethylanilines and Maleimides. The Journal of organic chemistry, 82(4), 1888-1894. https://doi.org/10.1021/acs.joc.6b03034
Guo, Jun-Tao, et al. "Chlorophyll-Catalyzed Visible-Light-Mediated Synthesis of Tetrahydroquinolines from N,N-Dimethylanilines and Maleimides." The Journal of organic chemistry vol. 82,4 (2017): 1888-1894. doi: https://doi.org/10.1021/acs.joc.6b03034
Guo JT, Yang DC, Guan Z, He YH. Chlorophyll-Catalyzed Visible-Light-Mediated Synthesis of Tetrahydroquinolines from N,N-Dimethylanilines and Maleimides. J Org Chem. 2017 Feb 17;82(4):1888-1894. doi: 10.1021/acs.joc.6b03034. Epub 2017 Feb 05. PMID: 28107007.
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Investigation of optical and thermal properties of N-(alkyl-substituted) maleimides for use in zero-zero-birefringence polymer.

Applied optics

Beppu S, Hotta H, Shafiee H, Tagaya A, Koike Y.
PMID: 25967788
Appl Opt. 2015 Feb 01;54(4):779-88. doi: 10.1364/AO.54.000779.

N-(alkyl-substituted) maleimides (RMIs) were proposed as materials useful for the development of a zero-zero-birefringence polymer that exhibits no birefringence. We analyzed the optical and thermal properties of poly(RMI)s, such as the refractive index, birefringence, and glass transition temperature. The...

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Beppu S, Hotta H, Shafiee H, et al. Investigation of optical and thermal properties of N-(alkyl-substituted) maleimides for use in zero-zero-birefringence polymer. Appl Opt. 2015;54(4):779-88doi: 10.1364/AO.54.000779.
Beppu, S., Hotta, H., Shafiee, H., Tagaya, A., & Koike, Y. (2015). Investigation of optical and thermal properties of N-(alkyl-substituted) maleimides for use in zero-zero-birefringence polymer. Applied optics, 54(4), 779-88. https://doi.org/10.1364/AO.54.000779
Beppu, Shotaro, et al. "Investigation of optical and thermal properties of N-(alkyl-substituted) maleimides for use in zero-zero-birefringence polymer." Applied optics vol. 54,4 (2015): 779-88. doi: https://doi.org/10.1364/AO.54.000779
Beppu S, Hotta H, Shafiee H, Tagaya A, Koike Y. Investigation of optical and thermal properties of N-(alkyl-substituted) maleimides for use in zero-zero-birefringence polymer. Appl Opt. 2015 Feb 01;54(4):779-88. doi: 10.1364/AO.54.000779. PMID: 25967788.
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Precision PEGylated polymers obtained by sequence-controlled copolymerization and postpolymerization modification.

Angewandte Chemie (International ed. in English)

Srichan S, Mutlu H, Badi N, Lutz JF.
PMID: 24990221
Angew Chem Int Ed Engl. 2014 Aug 25;53(35):9231-5. doi: 10.1002/anie.201403799. Epub 2014 Jul 02.

Copolymers containing water-soluble poly(ethylene glycol) (PEG) side chains and precisely controlled functional microstructures were synthesized by sequence-controlled copolymerization of donor and acceptor comonomers, that is, styrene derivatives and N-substituted maleimides. Two routes were compared for the preparation of these...

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Srichan S, Mutlu H, Badi N, et al. Precision PEGylated polymers obtained by sequence-controlled copolymerization and postpolymerization modification. Angew Chem Int Ed Engl. 2014;53(35):9231-5doi: 10.1002/anie.201403799.
Srichan, S., Mutlu, H., Badi, N., & Lutz, J. F. (2014). Precision PEGylated polymers obtained by sequence-controlled copolymerization and postpolymerization modification. Angewandte Chemie (International ed. in English), 53(35), 9231-5. https://doi.org/10.1002/anie.201403799
Srichan, Sansanee, et al. "Precision PEGylated polymers obtained by sequence-controlled copolymerization and postpolymerization modification." Angewandte Chemie (International ed. in English) vol. 53,35 (2014): 9231-5. doi: https://doi.org/10.1002/anie.201403799
Srichan S, Mutlu H, Badi N, Lutz JF. Precision PEGylated polymers obtained by sequence-controlled copolymerization and postpolymerization modification. Angew Chem Int Ed Engl. 2014 Aug 25;53(35):9231-5. doi: 10.1002/anie.201403799. Epub 2014 Jul 02. PMID: 24990221.
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A Mechanochromic Luminescent Dye Exhibiting On/Off Switching by Crystalline-Amorphous Transitions.

Chemistry, an Asian journal

Imoto H, Kizaki K, Naka K.
PMID: 26097088
Chem Asian J. 2015 Aug;10(8):1698-702. doi: 10.1002/asia.201500499. Epub 2015 Jul 07.

A mechanochromic luminescent dye based on a simple aminomaleimide skeleton was readily synthesized in a one-pot process. It exhibited an on/off mechanochromic luminescent switching property dependent on external stimuli, unlike a traditional mechanochromic color change. The green emission was...

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Imoto H, Kizaki K, Naka K. A Mechanochromic Luminescent Dye Exhibiting On/Off Switching by Crystalline-Amorphous Transitions. Chem Asian J. 2015;10(8):1698-702doi: 10.1002/asia.201500499.
Imoto, H., Kizaki, K., & Naka, K. (2015). A Mechanochromic Luminescent Dye Exhibiting On/Off Switching by Crystalline-Amorphous Transitions. Chemistry, an Asian journal, 10(8), 1698-702. https://doi.org/10.1002/asia.201500499
Imoto, Hiroaki, et al. "A Mechanochromic Luminescent Dye Exhibiting On/Off Switching by Crystalline-Amorphous Transitions." Chemistry, an Asian journal vol. 10,8 (2015): 1698-702. doi: https://doi.org/10.1002/asia.201500499
Imoto H, Kizaki K, Naka K. A Mechanochromic Luminescent Dye Exhibiting On/Off Switching by Crystalline-Amorphous Transitions. Chem Asian J. 2015 Aug;10(8):1698-702. doi: 10.1002/asia.201500499. Epub 2015 Jul 07. PMID: 26097088.
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Cobalt(III)-Catalyzed C-H Activation: Azo Directed Selective 1,4-Addition of Ortho C-H Bond to Maleimides.

The Journal of organic chemistry

Muniraj N, Prabhu KR.
PMID: 28560875
J Org Chem. 2017 Jul 07;82(13):6913-6921. doi: 10.1021/acs.joc.7b01094. Epub 2017 Jun 19.

Highly selective azo directed 1,4-addition of an ortho C-H bond to maleimides has been developed using Co(III) catalyst. This reaction furnishes 3-arylated succinimide derivatives in good yields with excellent selectivity. This protocol exhibits a broad substrate scope and is...

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Muniraj N, Prabhu KR. Cobalt(III)-Catalyzed C-H Activation: Azo Directed Selective 1,4-Addition of Ortho C-H Bond to Maleimides. J Org Chem. 2017;82(13):6913-6921doi: 10.1021/acs.joc.7b01094.
Muniraj, N., & Prabhu, K. R. (2017). Cobalt(III)-Catalyzed C-H Activation: Azo Directed Selective 1,4-Addition of Ortho C-H Bond to Maleimides. The Journal of organic chemistry, 82(13), 6913-6921. https://doi.org/10.1021/acs.joc.7b01094
Muniraj, Nachimuthu, and Prabhu, Kandikere Ramaiah. "Cobalt(III)-Catalyzed C-H Activation: Azo Directed Selective 1,4-Addition of Ortho C-H Bond to Maleimides." The Journal of organic chemistry vol. 82,13 (2017): 6913-6921. doi: https://doi.org/10.1021/acs.joc.7b01094
Muniraj N, Prabhu KR. Cobalt(III)-Catalyzed C-H Activation: Azo Directed Selective 1,4-Addition of Ortho C-H Bond to Maleimides. J Org Chem. 2017 Jul 07;82(13):6913-6921. doi: 10.1021/acs.joc.7b01094. Epub 2017 Jun 19. PMID: 28560875.
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The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide.

The Journal of organic chemistry

Roux MV, Jiménez P, Martín-Luengo MÁ, Dávalos JZ, Sun Z, Hosmane RS, Liebman JF.
PMID: 11671632
J Org Chem. 1997 May 02;62(9):2732-2737. doi: 10.1021/jo9621985.

In order to understand the antiaromaticity of maleimides, the enthalpies of formation and sublimation of N-methylmaleimide, N-methylsuccinimide, N-methylphthalimide, and N-benzoyl-N-methylbenzamide were measured. The numerical values of enthalpies of formation for these compounds in the solid state are -329.3 +/-...

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Roux MV, Jiménez P, Martín-Luengo MÁ, et al. The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide. J Org Chem. 1997;62(9):2732-2737doi: 10.1021/jo9621985.
Roux, M. V., Jiménez, P., Martín-Luengo MÁ, Dávalos, J. Z., Sun, Z., Hosmane, R. S., & Liebman, J. F. (1997). The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide. The Journal of organic chemistry, 62(9), 2732-2737. https://doi.org/10.1021/jo9621985
Roux, María Victoria, et al. "The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide." The Journal of organic chemistry vol. 62,9 (1997): 2732-2737. doi: https://doi.org/10.1021/jo9621985
Roux MV, Jiménez P, Martín-Luengo MÁ, Dávalos JZ, Sun Z, Hosmane RS, Liebman JF. The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide. J Org Chem. 1997 May 02;62(9):2732-2737. doi: 10.1021/jo9621985. PMID: 11671632.
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Tandem Aza.

Organic letters

Tailor J, Hall DG.
PMID: 11073683
Org Lett. 2000 Nov 16;2(23):3715-8. doi: 10.1021/ol006626b.

The alpha-hydroxyalkyl piperidine unit is common to several naturally occurring alkaloids and azasugar analogues. Polysubstituted piperidine derivatives of this kind (3), embodying four stereogenic centers, are formed in just a single operation from the highly stereocontrolled reaction of 4-borono-1-azadienes...

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Tailor J, Hall DG. Tandem Aza. Org Lett. 2000;2(23):3715-8doi: 10.1021/ol006626b.
Tailor, J., & Hall, D. G. (2000). Tandem Aza. Organic letters, 2(23), 3715-8. https://doi.org/10.1021/ol006626b
Tailor, and Hall. "Tandem Aza." Organic letters vol. 2,23 (2000): 3715-8. doi: https://doi.org/10.1021/ol006626b
Tailor J, Hall DG. Tandem Aza. Org Lett. 2000 Nov 16;2(23):3715-8. doi: 10.1021/ol006626b. PMID: 11073683.
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Synthesis of 6H-pyrrolo[3',4':2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold.

Organic & biomolecular chemistry

Lakatosh SA, Luzikov YN, Preobrazhenskaya MN.
PMID: 12929367
Org Biomol Chem. 2003 Mar 07;1(5):826-33. doi: 10.1039/b211163b.

Series of 3-arylalkyl- or 3-alkylamino-4-(indol-1-yl)maleimides and bis(indol-1-yl)maleimides were synthesised. The cyclization of the 3-substituted 4-(indol-1-yl)maleimides under the action of acids resulted in the formation of diazepine[1,4] derivatives with indoline and maleimide nuclei annelated. These compounds readily produced the corresponding...

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Lakatosh SA, Luzikov YN, Preobrazhenskaya MN. Synthesis of 6H-pyrrolo[3',4':2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold. Org Biomol Chem. 2003;1(5):826-33doi: 10.1039/b211163b.
Lakatosh, S. A., Luzikov, Y. N., & Preobrazhenskaya, M. N. (2003). Synthesis of 6H-pyrrolo[3',4':2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold. Organic & biomolecular chemistry, 1(5), 826-33. https://doi.org/10.1039/b211163b
Lakatosh, Sergey A, et al. "Synthesis of 6H-pyrrolo[3',4':2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold." Organic & biomolecular chemistry vol. 1,5 (2003): 826-33. doi: https://doi.org/10.1039/b211163b
Lakatosh SA, Luzikov YN, Preobrazhenskaya MN. Synthesis of 6H-pyrrolo[3',4':2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold. Org Biomol Chem. 2003 Mar 07;1(5):826-33. doi: 10.1039/b211163b. PMID: 12929367.
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Metal-induced supramolecular chirality in optically active polymers of oxazoline-substituted N-phenylmaleimides.

Chirality

Xi X, Jiang L, Sun W, Shen Z.
PMID: 17457832
Chirality. 2007 Jul;19(7):521-7. doi: 10.1002/chir.20369.

Polymerization of N-phenylmaleimide derivatives bearing a chiral oxazoline substituent at ortho-position on the phenyl group (namely, N-[o-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]maleimides, OPMI) was carried out with diethylzinc (Et2Zn) as an initiator. The resulting polymers exhibited a quite high specific rotation and a unique...

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Xi X, Jiang L, Sun W, et al. Metal-induced supramolecular chirality in optically active polymers of oxazoline-substituted N-phenylmaleimides. Chirality. 2007;19(7):521-7doi: 10.1002/chir.20369.
Xi, X., Jiang, L., Sun, W., & Shen, Z. (2007). Metal-induced supramolecular chirality in optically active polymers of oxazoline-substituted N-phenylmaleimides. Chirality, 19(7), 521-7. https://doi.org/10.1002/chir.20369
Xi, Xiujuan, et al. "Metal-induced supramolecular chirality in optically active polymers of oxazoline-substituted N-phenylmaleimides." Chirality vol. 19,7 (2007): 521-7. doi: https://doi.org/10.1002/chir.20369
Xi X, Jiang L, Sun W, Shen Z. Metal-induced supramolecular chirality in optically active polymers of oxazoline-substituted N-phenylmaleimides. Chirality. 2007 Jul;19(7):521-7. doi: 10.1002/chir.20369. PMID: 17457832.
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Effect of chirality on pi-stacking in styrene and maleimide alternating copolymers.

The journal of physical chemistry. B

Lazzara TD, Whitehead MA, van de Ven TG.
PMID: 18386866
J Phys Chem B. 2008 Apr 24;112(16):4892-9. doi: 10.1021/jp710172y. Epub 2008 Apr 03.

The effect of different chiral sequences in alternating copolymers of styrene and maleimide, poly(styrene-alt-dimethyl-N,N-propylamide) (SMI) was studied. The methods used for the SMI also applied to the general class of alternating copolymers of styrene and various maleimides. Only racemo-diisotactic...

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Lazzara TD, Whitehead MA, van de Ven TG. Effect of chirality on pi-stacking in styrene and maleimide alternating copolymers. J Phys Chem B. 2008;112(16):4892-9doi: 10.1021/jp710172y.
Lazzara, T. D., Whitehead, M. A., & van de Ven, T. G. (2008). Effect of chirality on pi-stacking in styrene and maleimide alternating copolymers. The journal of physical chemistry. B, 112(16), 4892-9. https://doi.org/10.1021/jp710172y
Lazzara, Thomas D, et al. "Effect of chirality on pi-stacking in styrene and maleimide alternating copolymers." The journal of physical chemistry. B vol. 112,16 (2008): 4892-9. doi: https://doi.org/10.1021/jp710172y
Lazzara TD, Whitehead MA, van de Ven TG. Effect of chirality on pi-stacking in styrene and maleimide alternating copolymers. J Phys Chem B. 2008 Apr 24;112(16):4892-9. doi: 10.1021/jp710172y. Epub 2008 Apr 03. PMID: 18386866.
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Showing 1 to 12 of 217 entries