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Organocatalytic Asymmetric Addition of Naphthols and Electron-Rich Phenols to Isatin-Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters

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Organocatalytic Asymmetric Addition of Naphthols and Electron-Rich Phenols to Isatin-Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters

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Montesinos Magraner, M.; Vila, C.; Cantón, R.; Blay, G.; Fernández, I.; Muñoz Roca, MDC.; Pedro, JR. (2015). Organocatalytic Asymmetric Addition of Naphthols and Electron-Rich Phenols to Isatin-Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters. Angewandte Chemie International Edition. 54(21):6320-6324. https://doi.org/10.1002/anie.201501273

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/72285

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Título: Organocatalytic Asymmetric Addition of Naphthols and Electron-Rich Phenols to Isatin-Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters
Autor: Montesinos Magraner, Marc Vila, Carlos Cantón, Rubén Blay, Gonzalo Fernández, Isabel Muñoz Roca, María del Carmen Pedro, José R.
Entidad UPV: Universitat Politècnica de València. Escuela Técnica Superior de Ingeniería del Diseño - Escola Tècnica Superior d'Enginyeria del Disseny
Fecha difusión:
Resumen:
A quinine-derived thiourea organocatalyst promoted the highly enantioselective addition of naphthols and activated phenols to ketimines derived from isatins. The reaction afforded chiral 3-amino-2-oxindoles with a ...[+]
Palabras clave: Asymmetric synthesis , Friedel-Crafts reactions , Isatin-derived ketimines , Naphthols , Organocatalysis
Derechos de uso: Cerrado
Fuente:
Angewandte Chemie International Edition. (issn: 1433-7851 ) (eissn: 1521-3773 )
DOI: 10.1002/anie.201501273
Editorial:
Wiley
Versión del editor: http://dx.doi.org/10.1002/anie.201501273
Código del Proyecto:
info:eu-repo/grantAgreement/MINECO//CTQ2013-47494-P/ES/NUEVOS RETOS EN EL DESARROLLO DE PROCESOS ENANTIOSELECTIVOS DE FORMACION DE ENLACES C-C MEDIANTE CATALISIS DUAL COOPERATIVA./
info:eu-repo/grantAgreement/GVA//ISIC2012%2F001/
Agradecimientos:
Financial support from the MINECO (Gobierno de Espana; CTQ2013-47494-P) and from Generalitat Valenciana (ISIC2012/001) is gratefully acknowledged. M.M.-M. thanks the Universitat de Valencia for a predoctoral grant. C.V. ...[+]
Tipo: Artículo

References

Kobayashi, S., Mori, Y., Fossey, J. S., & Salter, M. M. (2011). Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update. Chemical Reviews, 111(4), 2626-2704. doi:10.1021/cr100204f

Friestad, G. K., & Mathies, A. K. (2007). Recent developments in asymmetric catalytic addition to CN bonds. Tetrahedron, 63(12), 2541-2569. doi:10.1016/j.tet.2006.11.076

Uraguchi, D., Sorimachi, K., & Terada, M. (2004). Organocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan. Journal of the American Chemical Society, 126(38), 11804-11805. doi:10.1021/ja046185h [+]
Kobayashi, S., Mori, Y., Fossey, J. S., & Salter, M. M. (2011). Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update. Chemical Reviews, 111(4), 2626-2704. doi:10.1021/cr100204f

Friestad, G. K., & Mathies, A. K. (2007). Recent developments in asymmetric catalytic addition to CN bonds. Tetrahedron, 63(12), 2541-2569. doi:10.1016/j.tet.2006.11.076

Uraguchi, D., Sorimachi, K., & Terada, M. (2004). Organocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan. Journal of the American Chemical Society, 126(38), 11804-11805. doi:10.1021/ja046185h

Wang, Y.-Q., Song, J., Hong, R., Li, H., & Deng, L. (2006). Asymmetric Friedel−Crafts Reaction of Indoles with Imines by an Organic Catalyst. Journal of the American Chemical Society, 128(25), 8156-8157. doi:10.1021/ja062700v

Yu, P., He, J., & Guo, C. (2008). 9-Thiourea Cinchona alkaloid supported on mesoporous silica as a highly enantioselective, recyclable heterogeneous asymmetric catalyst. Chemical Communications, (20), 2355. doi:10.1039/b800640g

Kang, Q., Zhao, Z.-A., & You, S.-L. (2007). Highly Enantioselective Friedel−Crafts Reaction of Indoles with Imines by a Chiral Phosphoric Acid. Journal of the American Chemical Society, 129(6), 1484-1485. doi:10.1021/ja067417a

Terada, M., Yokoyama, S., Sorimachi, K., & Uraguchi, D. (2007). Chiral Phosphoric Acid-Catalyzed Enantioselective Aza-Friedel–Crafts Reaction of Indoles. Advanced Synthesis & Catalysis, 349(11-12), 1863-1867. doi:10.1002/adsc.200700151

Rowland, G. B., Rowland, E. B., Liang, Y., Perman, J. A., & Antilla, J. C. (2007). The Highly Enantioselective Addition of Indoles toN-Acyl Imines with Use of a Chiral Phosphoric Acid Catalyst. Organic Letters, 9(14), 2609-2611. doi:10.1021/ol0703579

Terada, M., & Sorimachi, K. (2007). Enantioselective Friedel−Crafts Reaction of Electron-Rich Alkenes Catalyzed by Chiral Brønsted Acid. Journal of the American Chemical Society, 129(2), 292-293. doi:10.1021/ja0678166

Zhang, G., Wang, L., Nie, J., & Ma, J. (2008). Chiral Brønsted Acid‐Mediated Enantioselective Organocatalytic Three‐Component Reaction for the Construction of Trifluoromethyl‐Containing Molecules. Advanced Synthesis & Catalysis, 350(10), 1457-1463. doi:10.1002/adsc.200800239

Kang, Q., Zheng, X.-J., & You, S.-L. (2008). Highly Enantioselective Friedel–Crafts Reaction of 4,7-Dihydroindoles with Imines by Chiral Phosphoric Acids: Facile Access to 2-Indolyl Methanamine Derivatives. Chemistry - A European Journal, 14(12), 3539-3542. doi:10.1002/chem.200800263

Enders, D., Seppelt, M., & Beck, T. (2010). Enantioselective Organocatalytic Synthesis of Arylglycines via Friedel-Crafts Alkylation of Arenes with a Glyoxylate Imine. Advanced Synthesis & Catalysis, 352(9), 1413-1418. doi:10.1002/adsc.201000143

Qian, Y., Ma, G., Lv, A., Zhu, H.-L., Zhao, J., & Rawal, V. H. (2010). Squaramide-catalyzed enantioselective Friedel–Crafts reaction of indoles with imines. Chemical Communications, 46(17), 3004. doi:10.1039/b922120d

Johannsen, M. (1999). An enantioselective synthesis of heteroaromatic N-tosyl α-amino acids. Chemical Communications, (21), 2233-2234. doi:10.1039/a906758b

Jia, Y.-X., Xie, J.-H., Duan, H.-F., Wang, L.-X., & Zhou, Q.-L. (2006). Asymmetric Friedel−Crafts Addition of Indoles toN-Sulfonyl Aldimines:  A Simple Approach to Optically Active 3-Indolyl-methanamine Derivatives. Organic Letters, 8(8), 1621-1624. doi:10.1021/ol0602001

Liu, L., Zhao, Q., Du, F., Chen, H., Qin, Z., & Fu, B. (2011). Highly enantioselective Friedel–Crafts reaction of indoles with N-sulfonyl aldimines catalyzed by heteroarylidene malonate-type bis(oxazoline) copper(II) complexes. Tetrahedron: Asymmetry, 22(20-22), 1874-1878. doi:10.1016/j.tetasy.2011.10.017

Wang, B.-L., Li, N.-K., Zhang, J.-X., Liu, G.-G., Liu, T., Shen, Q., & Wang, X.-W. (2011). Dinuclear zinc catalyzed asymmetric Friedel–Crafts amidoalkylation of indoles with aryl aldimines. Organic & Biomolecular Chemistry, 9(8), 2614. doi:10.1039/c0ob01200a

Jia, Y.-X., Zhong, J., Zhu, S.-F., Zhang, C.-M., & Zhou, Q.-L. (2007). Chiral Brønsted Acid Catalyzed Enantioselective Friedel–Crafts Reaction of Indoles and α-Aryl Enamides: Construction of Quaternary Carbon Atoms. Angewandte Chemie International Edition, 46(29), 5565-5567. doi:10.1002/anie.200701067

Jia, Y.-X., Zhong, J., Zhu, S.-F., Zhang, C.-M., & Zhou, Q.-L. (2007). Chiral Brønsted Acid Catalyzed Enantioselective Friedel–Crafts Reaction of Indoles and α-Aryl Enamides: Construction of Quaternary Carbon Atoms. Angewandte Chemie, 119(29), 5661-5663. doi:10.1002/ange.200701067

Husmann, R., Sugiono, E., Mersmann, S., Raabe, G., Rueping, M., & Bolm, C. (2011). Enantioselective Organocatalytic Synthesis of Quaternary α-Amino Acids Bearing a CF3Moiety. Organic Letters, 13(5), 1044-1047. doi:10.1021/ol103093r

Zhang, K.-F., Nie, J., Guo, R., Zheng, Y., & Ma, J.-A. (2013). Chiral Phosphoric Acid-Catalyzed Asymmetric Aza-Friedel-Crafts Reaction of Indoles with CyclicN-Acylketimines: Enantioselective Synthesis of Trifluoromethyldihydroquinazolines. Advanced Synthesis & Catalysis, 355(17), 3497-3502. doi:10.1002/adsc.201300534

Rueping, M., & Nachtsheim, B. (2009). Asymmetric Brønsted Acid Catalyzed Nucleophilic Addition to in situ Generated Chiral N-Acyliminium Ions. Synlett, 2010(01), 119-122. doi:10.1055/s-0029-1218539

Rueping, M., Raja, S., & Núñez, A. (2011). Asymmetric Brønsted Acid-Catalyzed Friedel-Crafts Reactions of Indoles with Cyclic Imines - Efficient Generation of Nitrogen-Substituted Quaternary Carbon Centers. Advanced Synthesis & Catalysis, 353(4), 563-568. doi:10.1002/adsc.201000952

Feng, J., Yan, W., Wang, D., Li, P., Sun, Q., & Wang, R. (2012). The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids. Chemical Communications, 48(64), 8003. doi:10.1039/c2cc33200k

Qian, Y., Jing, C., Zhai, C., & Hu, W. (2012). A Novel Method for Synthesizing N-Alkoxycarbonyl Aryl α-Imino Esters and Their Applications in Enantioselective Transformations. Advanced Synthesis & Catalysis, 354(2-3), 301-307. doi:10.1002/adsc.201100615

Brandes, S., Bella, M., Kjærsgaard, A., & Jørgensen, K. A. (2006). Chirally Aminated 2-Naphthols—Organocatalytic Synthesis of Non-Biaryl Atropisomers by Asymmetric Friedel–Crafts Amination. Angewandte Chemie International Edition, 45(7), 1147-1151. doi:10.1002/anie.200503042

Brandes, S., Bella, M., Kjærsgaard, A., & Jørgensen, K. A. (2006). Chirally Aminated 2-Naphthols—Organocatalytic Synthesis of Non-Biaryl Atropisomers by Asymmetric Friedel–Crafts Amination. Angewandte Chemie, 118(7), 1165-1169. doi:10.1002/ange.200503042

Brandes, S., Niess, B., Bella, M., Prieto, A., Overgaard, J., & Jørgensen, K. A. (2006). Non-Biaryl Atropisomers in Organocatalysis. Chemistry - A European Journal, 12(23), 6039-6052. doi:10.1002/chem.200600495

Wu, D., Zhang, X., Xu, Y., Xue, Y., Li, J., Wang, W., & Zhu, J. (2013). Organocatalytic Enantioselective Friedel-Crafts Reaction of 1-Naphthols with Isatins and an Unexpected Spontaneous Dehydration Process. Asian Journal of Organic Chemistry, 3(4), 480-486. doi:10.1002/ajoc.201300170

Kaur, J., Kumar, A., & Chimni, S. S. (2014). Organocatalytic asymmetric Friedel–Crafts reaction of 1-naphthols with isatins: an enantioselective synthesis of 3-aryl-3-hydroxy-2-oxindoles. Tetrahedron Letters, 55(13), 2138-2141. doi:10.1016/j.tetlet.2014.02.054

Liu, T.-Y., Cui, H.-L., Chai, Q., Long, J., Li, B.-J., Wu, Y., … Chen, Y.-C. (2007). Organocatalytic asymmetric Friedel–Crafts alkylation/cascade reactions of naphthols and nitroolefins. Chem. Commun., (22), 2228-2230. doi:10.1039/b704925k

Wang, X.-S., Yang, G.-S., & Zhao, G. (2008). Enantioselective synthesis of naphthopyran derivatives catalyzed by bifunctional thiourea-tertiary amines. Tetrahedron: Asymmetry, 19(6), 709-714. doi:10.1016/j.tetasy.2008.02.018

Wang, X.-S., Zheng, C.-W., Zhao, S.-L., Chai, Z., Zhao, G., & Yang, G.-S. (2008). Organocatalyzed Friedel–Craft-type reaction of 2-naphthol with β,γ-unsaturated α-keto ester to form novel optically active naphthopyran derivatives. Tetrahedron: Asymmetry, 19(23), 2699-2704. doi:10.1016/j.tetasy.2008.11.025

Hong, L., Wang, L., Sun, W., Wong, K., & Wang, R. (2009). Organocatalytic Asymmetric Friedel−Crafts Alkylation/Cyclization Cascade Reaction of 1-Naphthols and α,β-Unsaturated Aldehydes: An Enantioselective Synthesis of Chromanes and Dihydrobenzopyranes. The Journal of Organic Chemistry, 74(17), 6881-6884. doi:10.1021/jo901409d

Sohtome, Y., Shin, B., Horitsugi, N., Takagi, R., Noguchi, K., & Nagasawa, K. (2010). Entropy-Controlled Catalytic Asymmetric 1,4-Type Friedel-Crafts Reaction of Phenols Using Conformationally Flexible Guanidine/Bisthiourea Organocatalyst. Angewandte Chemie International Edition, 49(40), 7299-7303. doi:10.1002/anie.201003172

Sohtome, Y., Shin, B., Horitsugi, N., Takagi, R., Noguchi, K., & Nagasawa, K. (2010). Entropy-Controlled Catalytic Asymmetric 1,4-Type Friedel-Crafts Reaction of Phenols Using Conformationally Flexible Guanidine/Bisthiourea Organocatalyst. Angewandte Chemie, 122(40), 7457-7461. doi:10.1002/ange.201003172

Jiang, X., Wu, L., Xing, Y., Wang, L., Wang, S., Chen, Z., & Wang, R. (2012). Highly enantioselective Friedel–Crafts alkylation reaction catalyzed by rosin-derived tertiary amine–thiourea: synthesis of modified chromanes with anticancer potency. Chem. Commun., 48(3), 446-448. doi:10.1039/c1cc14379d

Paradisi, E., Righi, P., Mazzanti, A., Ranieri, S., & Bencivenni, G. (2012). Iminium ion catalysis: the enantioselective Friedel–Crafts alkylation–acetalization cascade of naphthols with α,β-unsaturated cyclic ketones. Chemical Communications, 48(91), 11178. doi:10.1039/c2cc35582e

Yu, L., Xie, X., Wu, S., Wang, R., He, W., Qin, D., … Jing, L. (2013). Organocatalytic asymmetric Michael addition of 2-naphthols to alkylideneindolenines generated in situ from arenesulfonylalkylindoles. Tetrahedron Letters, 54(28), 3675-3678. doi:10.1016/j.tetlet.2013.05.011

Liu, G., Zhang, S., Li, H., Zhang, T., & Wang, W. (2011). Organocatalytic Enantioselective Friedel−Crafts Reactions of 1-Naphthols with Aldimines. Organic Letters, 13(5), 828-831. doi:10.1021/ol102987n

Chauhan, P., & Chimni, S. S. (2011). Asymmetric Organocatalytic Aza-Friedel-Crafts Reaction of Naphthols with N-Sulfonyl Imines. European Journal of Organic Chemistry, 2011(9), 1636-1640. doi:10.1002/ejoc.201001653

Takizawa, S., Hirata, S., Murai, K., Fujioka, H., & Sasai, H. (2014). C3-Symmetric chiral trisimidazoline-catalyzed Friedel–Crafts (FC)-type reaction. Org. Biomol. Chem., 12(31), 5827-5830. doi:10.1039/c4ob00925h

Takizawa, S., Arteaga, F. A., Yoshida, Y., Kodera, J., Nagata, Y., & Sasai, H. (2013). Vanadium-catalyzed enantioselective Friedel–Crafts-type reactions. Dalton Trans., 42(33), 11787-11790. doi:10.1039/c2dt32202a

Szatmári, I., Martinek, T. A., Lázár, L., & Fülöp, F. (2004). Synthesis of 2,4-Diaryl-3,4-dihydro-2H-naphth[2,1-e][1,3]oxazines and Study of the Effects of the Substituents on Their Ring-Chain Tautomerism. European Journal of Organic Chemistry, 2004(10), 2231-2238. doi:10.1002/ejoc.200300753

M. Gerlach C. Maul PCT Int. Appl. 2001

Turgut, Z., Pelit, E., & Köycü, A. (2007). Synthesis of New 1,3-Disubstituted-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines. Molecules, 12(3), 345-352. doi:10.3390/12030345

Liu, D.-X., Zhang, L.-C., Wang, Q., Da, C.-S., Xin, Z.-Q., Wang, R., … Chan, A. S. C. (2001). The Application of Chiral Aminonaphthols in the Enantioselective Addition of Diethylzinc to Aryl Aldehydes. Organic Letters, 3(17), 2733-2735. doi:10.1021/ol016341e

Cimarelli, C., Palmieri, G., & Volpini, E. (2002). A practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde. Tetrahedron: Asymmetry, 13(22), 2417-2426. doi:10.1016/s0957-4166(02)00651-1

Ji, J.-X., Qiu, L.-Q., Yip, C. W., & Chan, A. S. C. (2003). A Convenient, One-Step Synthesis of Optically Active Tertiary Aminonaphthol and Its Applications in the Highly Enantioselective Alkenylations of Aldehydes. The Journal of Organic Chemistry, 68(4), 1589-1590. doi:10.1021/jo026551k

Dong, Y., Sun, J., Wang, X., Xu, X., Cao, L., & Hu, Y. (2004). Highly regioselective N-alkylation of nonracemic Betti base: a novel one-pot synthesis of chiral N-methyl-N-alkyl Betti bases. Tetrahedron: Asymmetry, 15(10), 1667-1672. doi:10.1016/j.tetasy.2004.04.006

Wang, X., Dong, Y., Sun, J., Xu, X., Li, R., & Hu, Y. (2005). Nonracemic Betti Base as a New Chiral Auxiliary:  Application to Total Syntheses of Enantiopure (2S,6R)-Dihydropinidine and (2S,6R)-Isosolenopsins. The Journal of Organic Chemistry, 70(5), 1897-1900. doi:10.1021/jo0480444

Dounay, A. B., & Overman, L. E. (2003). The Asymmetric Intramolecular Heck Reaction in Natural Product Total Synthesis. Chemical Reviews, 103(8), 2945-2964. doi:10.1021/cr020039h

Marti, C., & Carreira, E. M. (2003). Construction of Spiro[pyrrolidine-3,3′-oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids. European Journal of Organic Chemistry, 2003(12), 2209-2219. doi:10.1002/ejoc.200300050

Galliford, C. V., & Scheidt, K. A. (2007). Pyrrolidinyl-Spirooxindole Natural Products as Inspirations for the Development of Potential Therapeutic Agents. Angewandte Chemie International Edition, 46(46), 8748-8758. doi:10.1002/anie.200701342

Galliford, C. V., & Scheidt, K. A. (2007). Natürliche Pyrrolidinylspirooxindole als Vorlagen für die Entwicklung medizinischer Wirkstoffe. Angewandte Chemie, 119(46), 8902-8912. doi:10.1002/ange.200701342

Zhou, F., Liu, Y.-L., & Zhou, J. (2010). Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C-3 Position. Advanced Synthesis & Catalysis, 352(9), 1381-1407. doi:10.1002/adsc.201000161

Klein, J. E. M. N., & Taylor, R. J. K. (2011). Transition-Metal-Mediated Routes to 3,3-Disubstituted Oxindoles through Anilide Cyclisation. European Journal of Organic Chemistry, 2011(34), 6821-6841. doi:10.1002/ejoc.201100836

Shen, K., Liu, X., Lin, L., & Feng, X. (2012). Recent progress in enantioselective synthesis of C3-functionalized oxindoles: rare earth metals take action. Chem. Sci., 3(2), 327-334. doi:10.1039/c1sc00544h

Bernard, K., Bogliolo, S., & Ehrenfeld, J. (2005). Vasotocin and vasopressin stimulation of the chloride secretion in the human bronchial epithelial cell line, 16HBE14o-. British Journal of Pharmacology, 144(8), 1037-1050. doi:10.1038/sj.bjp.0706103

Oost, T., Backfisch, G., Bhowmik, S., van Gaalen, M. M., Geneste, H., Hornberger, W., … Wernet, W. (2011). Potent and selective oxindole-based vasopressin 1b receptor antagonists with improved pharmacokinetic properties. Bioorganic & Medicinal Chemistry Letters, 21(12), 3828-3831. doi:10.1016/j.bmcl.2011.03.012

Decaux, G., Soupart, A., & Vassart, G. (2008). Non-peptide arginine-vasopressin antagonists: the vaptans. The Lancet, 371(9624), 1624-1632. doi:10.1016/s0140-6736(08)60695-9

Shimazaki, T., Iijima, M., & Chaki, S. (2006). The pituitary mediates the anxiolytic-like effects of the vasopressin V1B receptor antagonist, SSR149415, in a social interaction test in rats. European Journal of Pharmacology, 543(1-3), 63-67. doi:10.1016/j.ejphar.2006.06.032

Ochi, M., Kawasaki, K., Kataoka, H., Uchio, Y., & Nishi, H. (2001). AG-041R, a Gastrin/CCK-B Antagonist, Stimulates Chondrocyte Proliferation and Metabolism in Vitro. Biochemical and Biophysical Research Communications, 283(5), 1118-1123. doi:10.1006/bbrc.2001.4911

Rottmann, M., McNamara, C., Yeung, B. K. S., Lee, M. C. S., Zou, B., Russell, B., … Diagana, T. T. (2010). Spiroindolones, a Potent Compound Class for the Treatment of Malaria. Science, 329(5996), 1175-1180. doi:10.1126/science.1193225

Yeung, B. K. S., Zou, B., Rottmann, M., Lakshminarayana, S. B., Ang, S. H., Leong, S. Y., … Keller, T. H. (2010). Spirotetrahydro β-Carbolines (Spiroindolones): A New Class of Potent and Orally Efficacious Compounds for the Treatment of Malaria. Journal of Medicinal Chemistry, 53(14), 5155-5164. doi:10.1021/jm100410f

Chauhan, P., & Chimni, S. S. (2013). Organocatalytic asymmetric synthesis of 3-amino-2-oxindole derivatives bearing a tetra-substituted stereocenter. Tetrahedron: Asymmetry, 24(7), 343-356. doi:10.1016/j.tetasy.2013.03.002

Cheng, L., Liu, L., Wang, D., & Chen, Y.-J. (2009). Highly Enantioselective and Organocatalytic α-Amination of 2-Oxindoles. Organic Letters, 11(17), 3874-3877. doi:10.1021/ol901405r

Qian, Z.-Q., Zhou, F., Du, T.-P., Wang, B.-L., Ding, M., Zhao, X.-L., & Zhou, J. (2009). Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of 3-substituted oxindoles. Chemical Communications, (44), 6753. doi:10.1039/b915257a

Bui, T., Borregan, M., & Barbas, C. F. (2009). Expanding the Scope of Cinchona Alkaloid-Catalyzed Enantioselective α-Aminations of Oxindoles: A Versatile Approach to Optically Active 3-Amino-2-oxindole Derivatives. The Journal of Organic Chemistry, 74(23), 8935-8938. doi:10.1021/jo902039a

Mouri, S., Chen, Z., Mitsunuma, H., Furutachi, M., Matsunaga, S., & Shibasaki, M. (2010). Catalytic Asymmetric Synthesis of 3-Aminooxindoles: Enantiofacial Selectivity Switch in Bimetallic vs Monometallic Schiff Base Catalysis. Journal of the American Chemical Society, 132(4), 1255-1257. doi:10.1021/ja908906n

Bui, T., Hernández-Torres, G., Milite, C., & Barbas, C. F. (2010). Highly Enantioselective Organocatalytic α-Amination Reactions of Aryl Oxindoles: Developing Designer Multifunctional Alkaloid Catalysts. Organic Letters, 12(24), 5696-5699. doi:10.1021/ol102493q

Zhou, F., Ding, M., Liu, Y.-L., Wang, C.-H., Ji, C.-B., Zhang, Y.-Y., & Zhou, J. (2011). Organocatalytic Asymmetric α-Amination of Unprotected 3-Aryl and 3-Aliphatic Substituted Oxindoles using Di-tert-butyl Azodicarboxylate. Advanced Synthesis & Catalysis, 353(16), 2945-2952. doi:10.1002/adsc.201100379

Shen, K., Liu, X., Wang, G., Lin, L., & Feng, X. (2011). Facile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3-Hydroxyamino-2-Oxindoles Using Nitrosoarenes. Angewandte Chemie International Edition, 50(20), 4684-4688. doi:10.1002/anie.201100758

Shen, K., Liu, X., Wang, G., Lin, L., & Feng, X. (2011). Facile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3-Hydroxyamino-2-Oxindoles Using Nitrosoarenes. Angewandte Chemie, 123(20), 4780-4784. doi:10.1002/ange.201100758

Zhou, F., Zeng, X.-P., Wang, C., Zhao, X.-L., & Zhou, J. (2013). Organocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at the C3 position. Chemical Communications, 49(20), 2022. doi:10.1039/c3cc38819k

Zhang, T., Cheng, L., Liu, L., Wang, D., & Chen, Y.-J. (2010). Asymmetric organocatalytic N-nitroso-aldol reaction of oxindoles. Tetrahedron: Asymmetry, 21(23), 2800-2806. doi:10.1016/j.tetasy.2010.11.002

Jia, L.-N., Huang, J., Peng, L., Wang, L.-L., Bai, J.-F., Tian, F., … Wang, L.-X. (2012). Asymmetric hydroxyamination of oxindoles catalyzed by chiral bifunctional tertiary aminethiourea: construction of 3-amino-2-oxindoles with quaternary stereocenters. Org. Biomol. Chem., 10(2), 236-239. doi:10.1039/c1ob06413d

Companyó, X., Valero, G., Pineda, O., Calvet, T., Font-Bardía, M., Moyano, A., & Rios, R. (2012). Enantioselective organocatalytic oxyamination of unprotected 3-substituted oxindoles. Org. Biomol. Chem., 10(2), 431-439. doi:10.1039/c1ob06503c

Hara, N., Nakamura, S., Sano, M., Tamura, R., Funahashi, Y., & Shibata, N. (2012). Enantioselective Synthesis of AG-041R by using N-Heteroarenesulfonyl Cinchona Alkaloid Amides as Organocatalysts. Chemistry - A European Journal, 18(30), 9276-9280. doi:10.1002/chem.201200367

Yan, W., Wang, D., Feng, J., Li, P., Zhao, D., & Wang, R. (2012). Synthesis of N-Alkoxycarbonyl Ketimines Derived from Isatins and Their Application in Enantioselective Synthesis of 3-Aminooxindoles. Organic Letters, 14(10), 2512-2515. doi:10.1021/ol3007953

Li, T.-Z., Wang, X.-B., Sha, F., & Wu, X.-Y. (2014). Organocatalyzed Enantioselective Mannich Reaction of Pyrazoleamides with Isatin-Derived Ketimines. The Journal of Organic Chemistry, 79(10), 4332-4339. doi:10.1021/jo500145w

Wang, X.-B., Li, T.-Z., Sha, F., & Wu, X.-Y. (2013). Enantioselective Squaramide-Catalysed Domino Mannich-Cyclization Reaction of Isatin Imines. European Journal of Organic Chemistry, 2014(4), 739-744. doi:10.1002/ejoc.201301350

Zhao, J., Fang, B., Luo, W., Hao, X., Liu, X., Lin, L., & Feng, X. (2014). Enantioselective Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Silyl Ketene Imines with Isatin-Derived Ketimines. Angewandte Chemie International Edition, 54(1), 241-244. doi:10.1002/anie.201408730

Zhao, J., Fang, B., Luo, W., Hao, X., Liu, X., Lin, L., & Feng, X. (2014). Enantioselective Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Silyl Ketene Imines with Isatin-Derived Ketimines. Angewandte Chemie, 127(1), 243-246. doi:10.1002/ange.201408730

Liu, Y.-L., Zhou, F., Cao, J.-J., Ji, C.-B., Ding, M., & Zhou, J. (2010). A facile method for the synthesis of oxindole based quaternary α-aminonitriles via the Strecker reaction. Organic & Biomolecular Chemistry, 8(17), 3847. doi:10.1039/c0ob00174k

Liu, Y.-L., & Zhou, J. (2013). Organocatalytic asymmetric cyanation of isatin derived N-Boc ketoimines. Chem. Commun., 49(39), 4421-4423. doi:10.1039/c2cc36665g

Arai, T., Matsumura, E., & Masu, H. (2014). Bis(imidazolidine)pyridine-NiCl2 Catalyst for Nitro-Mannich Reaction of Isatin-Derived N-Boc Ketimines: Asymmetric Synthesis of Chiral 3-Substituted 3-Amino-2-oxindoles. Organic Letters, 16(10), 2768-2771. doi:10.1021/ol501085y

Holmquist, M., Blay, G., & Pedro, J. R. (2014). Highly enantioselective aza-Henry reaction with isatin N-Boc ketimines. Chem. Commun., 50(66), 9309-9312. doi:10.1039/c4cc04051a

Kumar, A., Kaur, J., Chimni, S. S., & Jassal, A. K. (2014). Organocatalytic enantioselective aza-Henry reaction of ketimines derived from isatins: access to optically active 3-amino-2-oxindoles. RSC Adv., 4(47), 24816-24819. doi:10.1039/c4ra00902a

Wang, Y.-H., Liu, Y.-L., Cao, Z.-Y., & Zhou, J. (2014). An Organocatalytic Addition of Nitromethane to Activated Ketimines. Asian Journal of Organic Chemistry, 3(4), 429-432. doi:10.1002/ajoc.201300289

Lv, H., Tiwari, B., Mo, J., Xing, C., & Chi, Y. R. (2012). Highly Enantioselective Addition of Enals to Isatin-Derived Ketimines Catalyzed by N-Heterocyclic Carbenes: Synthesis of Spirocyclic γ-Lactams. Organic Letters, 14(21), 5412-5415. doi:10.1021/ol302475g

Hu, F.-L., Wei, Y., Shi, M., Pindi, S., & Li, G. (2013). Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers. Organic & Biomolecular Chemistry, 11(12), 1921. doi:10.1039/c3ob27495k

Nakamura, S., Hyodo, K., Nakamura, M., Nakane, D., & Masuda, H. (2013). Catalytic Enantioselective Allylation of Ketimines by Using Palladium Pincer Complexes with Chiral Bis(imidazoline)s. Chemistry - A European Journal, 19(23), 7304-7309. doi:10.1002/chem.201300685

Xu, J., Mou, C., Zhu, T., Song, B.-A., & Chi, Y. R. (2014). N-Heterocyclic Carbene-Catalyzed Chemoselective Cross-Aza-Benzoin Reaction of Enals with Isatin-Derived Ketimines: Access to Chiral Quaternary Aminooxindoles. Organic Letters, 16(12), 3272-3275. doi:10.1021/ol501286e

George, J., Sridhar, B., & Reddy, B. V. S. (2014). First example of quinine-squaramide catalyzed enantioselective addition of diphenyl phosphite to ketimines derived from isatins. Organic & Biomolecular Chemistry, 12(10), 1595. doi:10.1039/c3ob42026d

Blay, G., Fernández, I., Monleón, A., Pedro, J. R., & Vila, C. (2009). Enantioselective Zirconium-Catalyzed Friedel−Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones. Organic Letters, 11(2), 441-444. doi:10.1021/ol802509m

Blay, G., Fernández, I., Muñoz, M. C., Pedro, J. R., Recuenco, A., & Vila, C. (2011). Enantioselective Synthesis of Tertiary Alcohols through a Zirconium-Catalyzed Friedel–Crafts Alkylation of Pyrroles with α-Ketoesters. The Journal of Organic Chemistry, 76(15), 6286-6294. doi:10.1021/jo2010704

Tian, S.-K., Chen, Y., Hang, J., Tang, L., McDaid, P., & Deng, L. (2004). Asymmetric Organic Catalysis with Modified Cinchona Alkaloids. Accounts of Chemical Research, 37(8), 621-631. doi:10.1021/ar030048s

Marcelli, T., & Hiemstra, H. (2010). Cinchona Alkaloids in Asymmetric Organocatalysis. Synthesis, 2010(08), 1229-1279. doi:10.1055/s-0029-1218699

Connon, S. J. (2006). Organocatalysis Mediated by (Thio)urea Derivatives. Chemistry - A European Journal, 12(21), 5418-5427. doi:10.1002/chem.200501076

Alemán, J., Parra, A., Jiang, H., & Jørgensen, K. A. (2011). Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis. Chemistry - A European Journal, 17(25), 6890-6899. doi:10.1002/chem.201003694

Song, J., Wang, Y., & Deng, L. (2006). The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids:  Enantioselective Synthesis of β-Amino Acids. Journal of the American Chemical Society, 128(18), 6048-6049. doi:10.1021/ja060716f

Bernardi, L., Fini, F., Herrera, R. P., Ricci, A., & Sgarzani, V. (2006). Enantioselective aza-Henry reaction using cinchona organocatalysts. Tetrahedron, 62(2-3), 375-380. doi:10.1016/j.tet.2005.09.076

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Chauhan, P., & Chimni, S. S. (2013). Organocatalytic enantioselective aza-Friedel–Crafts reaction of sesamols with N-sulfonylimines catalyzed by 6′-OH Cinchona alkaloids. Tetrahedron Letters, 54(35), 4613-4616. doi:10.1016/j.tetlet.2013.06.032

Bai, S., Liao, Y., Lin, L., Luo, W., Liu, X., & Feng, X. (2014). N,N′-Dioxide–Scandium(III)-Catalyzed Asymmetric Aza-Friedel–Crafts Reaction of Sesamol with Aldimines. The Journal of Organic Chemistry, 79(21), 10662-10668. doi:10.1021/jo5020036

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