Recent Progress on the Construction of Chiral 3-Amino-2-oxindoles Skeleton with Isatin-Derived Ketimines as Reactants
- Corresponding author: JIN Ying, 1364603451@qq.com JIANHG Yingzi, yzjiang@ybu.edu.cn
Citation:
ZHANG Junwei, WU Hao, CHEN Zhe, JIN Ying, JIANHG Yingzi. Recent Progress on the Construction of Chiral 3-Amino-2-oxindoles Skeleton with Isatin-Derived Ketimines as Reactants[J]. Chinese Journal of Applied Chemistry,
;2019, 36(12): 1343-1360.
doi:
10.11944/j.issn.1000-0518.2019.12.190170
Jasneet K, Swapandeep S C. Catalytic Synthesis of 3-Aminooxindoles via Addition to Isatin Imine:An Update[J]. Org Biomol Chem, 2018,16(18):3328-3347. doi: 10.1039/C7OB03002A
Cao Z Y, Zhou F, Zhou J. Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3, 3-Disubstituted Oxindoles[J]. Acc Chem Res, 2018,51(6):1443-1454. doi: 10.1021/acs.accounts.8b00097
Fang B, Liu X H, Zhao J N. Chiral Bifunctional Guanidine-Catalyzed Enantioselective Aza-Henry Reaction of Isatin-Derived Ketimines[J]. J Org Chem, 2015,80(6):3332-3338. doi: 10.1021/acs.joc.5b00075
Hu Y, Zhou Z J, Gong L. Asymmetric aza-Henry Reaction to Provide Oxindoles with Quaternary Carbon Stereocenter Catalyzed by a Metal-Templated Chiral Brønsted Base[J]. Org Chem Front, 2015,2(8):968-972. doi: 10.1039/C5QO00132C
Sivamuthuraman K, Kesavan V. Stereodivergent Synthesis of 3-Aminooxindole Derivatives Containing Vicinal Tetrasubstituted Stereocenters via the Mannich Reaction[J]. J Org Chem, 2018,83(16):8936-8952. doi: 10.1021/acs.joc.8b01020
Zhu J Y, Yang W L, Liu Y Z. Copper(Ⅰ)-catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases with Isatin-Derived Ketimines:Enantioselective Synthesis of 3-Substituted 3-Aminooxindoles[J]. Org Chem Front, 2018,5(1):70-74.
Kuwano S, Suzuki T, Hosaka Y. A Chiral Organic Base Catalyst with Halogen-Bonding-Donor Functionality:Asymmetric Mannich Reactions of Malononitrile with N-Boc Aldimines and Ketimines[J]. Chem Commun, 2018,54(31):3847-3850. doi: 10.1039/C8CC00865E
Han X Y, Chan W L, Yao W J. Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates[J]. Angew Chem Int Ed, 2016,55(22):6492-6496. doi: 10.1002/anie.201600453
Gui H Z, Gao Y N, Wei Y, et al. Highly Efficient and Diastereoselective Construction of Trifluoromethyl-Containing Spiro[pyrrolidin-3, 2'-oxindole] by a Catalyst-free Mutually Activated[3+2] Cycloaddition Reaction[J/OL]. Chem Eur J, 2018, 24(40): 10038-10043.
Xu P W, Yu J S, Chen C. Catalytic Enantioselective Construction of Spiro Quaternary Carbon Stereocenters[J]. ACS Catal, 2019,9(3):1820-1882. doi: 10.1021/acscatal.8b03694
Pellissier H. Synthesis of Chiral 3-Substituted 3-Amino-2-Oxindoles Through Enantioselective Catalytic Nucleophilic Additions to Isatin Imines[J]. Beilstein J Org Chem, 2018,14:1349-1369. doi: 10.3762/bjoc.14.114
LIU Jing. Research on Chirall Construction of 3, 3'-Disubstituted Oxindole Derivatives with Poteneial Bioactivity[D]. Zhejiang: China Jiliang University, 2017(in Chinese).
Hajra S, Jana B. Quinine-Based Trifunctional Organocatalyst for Tandem Aza-Henry Reaction-Cyclization:Asymmetric Synthesis of Spiroxindole-Pyrrolidine/Piperidines[J]. Org Lett, 2017,19(18):4778-4781. doi: 10.1021/acs.orglett.7b02150
WANG Yuhui, ZHOU Jian. Asymmetric aza-Henry Reaction of Isatin Ketimines[C]//The 8th National Molecular Chiral Symposium of the Chinese Chemical Society. Chinese Chemical Society: Chinese Chemical Society, 2017: 91(in Chinese).
Liu Y X, Liu Y, Wang J D. Asymmetric Phase-Transfer Catalysts Bearing Multiple Hydrogen-Bonding Donors:Synthesis and Application In Nitro-Mannich Reaction of Isatin-Derived N-Boc Ketimines[J]. Tetrahedron, 2017,58(24):2400-2403. doi: 10.1016/j.tetlet.2017.05.022
Wang J D, Liu Y, Liu Y X. L-tert-Leucine Derived Urea-Ammonium Salts:Efficient Bifunctional Phase Transfer Catalysts for Highly Diastereo- and Enantioselective Aza-Henry Reaction of Isatin Derived N-Boc Ketimines with Α-Aryl Nitromethanes[J]. Tetrahedron, 2019,75(20):2883-2992. doi: 10.1016/j.tet.2019.04.015
Menapara T, Tak R, Chinnaraja E. Chiral Cu(Ⅱ)-N 4 Complex Catalyzed Asymmetric Aza-Henry Reaction and Its Application in the Synthesis of β-Diamine[J]. Chemistry Select, 2017,2(14):4063-4067.
Menapara T, Tak R, Saravanan S. Isatin N-Protected Ketimines with Nitromethane Catalyzed by Chiral Binol Linked Monomeric Macrocyclic Cu(Ⅱ)esalen Complex[J]. Tetrahedron, 2018,74(49):7000-7008. doi: 10.1016/j.tet.2018.10.001
Lv H, Tiwari B, Mo J. Highly Enantioselective Addition of Enals to Isatin-Derived Ketimines Catalyzed by N-Heterocyclic Carbenes:Synthesis of Spirocyclic γ-Lactams[J]. Org Lett, 2012,14(21):5412-5415. doi: 10.1021/ol302475g
Qian Y L, Xia P J, Li J. Diversity-Driven and Facile 1, 3-Dipolar Cycloaddition to Access Dispirooxindole Imidazolidine Scaffolds[J]. Org Biomol Chem, 2017,15(41):8705-8708. doi: 10.1039/C7OB02319G
Rainoldi G, Faltracco M, Spatti C. Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines[J]. Molecules, 2017,22(11):1-13.
Xu J F, Yuan S R, Peng J Y. Enantioselective[2+2] Annulation of Simple Aldehydes with Isatin-Derived Ketimines via Oxidative N-Heterocyclic Carbene Catalysis[J]. Chem Commun, 2017,53(24):3430-3433. doi: 10.1039/C7CC01232B
Guo S S, Dong P, Chen Y S. Chiral Guanidine/Copper Catalyzed Asymmetric Azide-Alkyne Cycloaddition/[2++2] Cascade Reaction[J]. Angew Chem Int Ed, 2018,57(51):16852-16856. doi: 10.1002/anie.201810679
Jin J H, Zhao J H, Yang W L. Asymmetric Synthesis of Spirooxindole β-Lactams via Isothiourea-Catalyzed Mannich/lactamization Reaction of Aryl Acetic Acids with Isatin-Derived Ketimines[J]. Adv Synth Catal, 2019,361(7):1592-1596. doi: 10.1002/adsc.201801621
Huang W J, Chen Q, Lin N. Asymmetric Synthesis of Trifluoromethyl-Substituted 3, 3'-Pyrrolidinyl-Dispirooxindoles Through Organocatalytic 1, 3-Dipolar Cycloaddition Reactions[J]. Org Chem Front, 2017,4(3):472-482. doi: 10.1039/C6QO00723F
Zhu W R, Zhang Z W, Huang W H. Asymmetric Synthesis of Vicinally Bis(trifluoromethyl)-Substituted 3, 3'-Pyrrolidinyl Spirooxindoles via Organocatalytic 1, 3-Dipolar Cycloaddition Reactions[J]. Synthesis, 2019,51(9):1969-1979. doi: 10.1055/s-0037-1612089
Bao X Z, Wei S Q, Qian X K. Asymmetric Construction of a Multi-Pharmacophore-Containing Dispirotriheterocyclic Scaffold and Identification of a Human Carboxylesterase 1 Inhibitor[J]. Org Lett, 2018,20(11):3394-3398. doi: 10.1021/acs.orglett.8b01316
You Y, Lu W Y, Wang Z H. Organocatalytic Asymmetric[3+2] Cycloaddition of N-2, 2, 2-Trifluoroethylisatin Ketimines with β-Trifluoromethyl Electrondeficient Alkenes:Access to Vicinally Bis(trifluoromethyl)-Substituted 3, 2'-Pyrrolidinyl Spirooxindoles[J]. Org Lett, 2018,20(11):4453-4457.
Song Y X, Du D M. Asymmetric Construction of Bispiro[oxindole-pyrrolidine-rhodanine]s via Squaramide-Catalyzed Domino Michael/Mannich[3+2] Cycloaddition of Rhodanine Derivatives with N-(2, 2, 2-Trifluoroethyl)isatin Ketimines[J]. J Org Chem, 2018,83(16):9278-9290. doi: 10.1021/acs.joc.8b01245
Lin Y, Song Y X, Du D M. Enantioselective Synthesis of CF3-Containing 3, 2'-Pyrrolidinyl Spirooxindoles and Dispirooxindoles via Thiourea-Catalyzed Domino Michael/Mannich[3+2] Cycloaddition Reactions[J]. Adv Synth Catal, 2019,361(5):1064-1070. doi: 10.1002/adsc.201801608
Zhao X Y, Xiong J L, An J K. Diastereodivergent Construction of Bispiro[oxindole-bi-pyrrolidines]s with Four Consecutive Stereocenters via Asymmetric[3+2] Cycloaddition of 2, 3-dioxopyrrolidines by Identical Catalysts[J]. Org Chem Front, 2019. doi: 10.1039/C9QO00452A
Zhi Y, Zhao K, Essen C V. Thiourea-Catalyzed Domino Michael-Mannich[3+2] Cycloadditions:A Strategy for the Asymmetric Synthesis of 3, 3'-Pyrro-lidinyl-dispirooxindoles[J]. Synlett, 2017,28(20):2876-2880. doi: 10.1055/s-0036-1589070
He Q, Du W, Chen Y C. Asymmetric[3+2] Annulations to Construct 1, 2-Bispirooxindoles Incorporating a Dihydropyrrolidine Motif[J]. Adv Synth Catal, 2017,359(21):3782-3791. doi: 10.1002/adsc.201700849
Wu X Y, Gao Y N, Shi M. Phosphine-Catalyzed[3+2] Annulation of N-2, 2, 2-Trifluoroethylisatin Ketimines with γ-Substituted Allenoates:Synthesis of Spiro[indoline-3, 2'-pyrrole[J]. Eur J Org Chem, 2019,7:1620-1626.
Huang X B, Li X J, Li T T. Palladium-Catalyzed Highly Enantioselective Cycloaddition of Vinyl Cyclopropanes with Imines[J]. Org Lett, 2019,21(6):1713-1716. doi: 10.1021/acs.orglett.9b00274
Akaev A A, Bezzubov S I, Desyatkin V G. Stereocontrolled[3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles:Access to Spiro[oxindole-3, 2'-pyrrolidines[J]. J Org Chem, 2019,84(6):3340-3356. doi: 10.1021/acs.joc.8b03208
Xu J F, Yuan S R, Miao M Z. N-Heterocyclic Carbene Catalyzed[4+2] Annulation Reactions with in Situ Generated Heterocyclic ortho-Quinodimethanes[J]. Org Lett, 2016,18(15):3822-3825. doi: 10.1021/acs.orglett.6b01831
Carlos V, Alejandra R P, Marc M M. Organocatalytic Enantioselective Functionalization of Hydroxyquinolines Through an Aza-Friedel-Crafts Alkylation with Isatin-Derived Ketimines[J]. Adv Synth Catal, 2018,360(5):859-864. doi: 10.1002/adsc.201701217
WANG Liming, LIN Geng, ZHAO Meijun. Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines[J]. Chinese J Org Chem, 2018,38(3):642-647.
WANG Liming, CHANG Sheng, JIN Ying. Cinchona Alkaloid Derivatives Catalyzed Asymmetric aza-Friedel-Crafts Reaction of β-Naphthol with Tosylimines[J]. J Mol Catal(China), 2013,27(6):502-506.
HOU Yadong, PANG Haixia, YANG Chao. Mesoporous MCM-41 Supported Schiff Base-Cu(ClO4)2·6H2O Catalyzed Synthesis of Spiro[indole-thiazolidine] Derivatives[J]. Chinese J Org Chem, 2018,38(8):2036-2044.
Wang Q H, Zhu Z X, Huang T. Base Catalyzed Unexpected Rearrangement of Isatin-Derived N, N'-Cyclic Azomethine Imines and Michael Addition to Hindered Vinylidene Bisphosphonates:Access to 3, 3-Disubstituted Oxindole-Fused Pyrazolidin-3-One Derivatives Containing Bisphosphonates[J]. Tetrahedron, 2019,75(3):416-421. doi: 10.1016/j.tet.2018.12.014
Hu F L, Wei Y, Shi M. Asymmetric Catalytic aza-Morita-Baylis-Hillman Reaction for the Synthesis of 3-Substituted-3-Aminooxindoles with Chiral Quaternary Carbon Centers[J]. Org Biomol Chem, 2013,11(12):1921-1924. doi: 10.1039/c3ob27495k
Choudhary M K, Menapara T, Tak R. Asymmetric Synthesis of 3-Amino Oxindoles Using Isatin-Derived N-Boc Ketimines with Activated Nitroolefin Catalyzed by Organocatalysts[J]. ChemistrySelect, 2017,2(7):2224-2229. doi: 10.1002/slct.201700032
Li T Z, Wang X B, Sha F. Catalytic Enantioselective Addition of Alcohols to Isatin-Derived N-Boc Ketimines[J]. Tetrahedron, 2013,69(35):7314-7319. doi: 10.1016/j.tet.2013.06.076
Arai T, Tsuchiya K, Matsumura E. PyBidine-NiCl2-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines[J]. Org Lett, 2015,17(10):2416-2419. doi: 10.1021/acs.orglett.5b00928
Liu J, Zhu F M, Chu Y B. The 2'-Phenyl Cinchonidine Thiourea-Catalyzed Asymmetric Addition of Alcohols to Isatin-Derived N-Boc Ketimines[J]. Tetrahedron:Asymm, 2015,26:1130-1137. doi: 10.1016/j.tetasy.2015.08.011
Lu J, Sha F, Wu X Y. Copper-Catalyzed Enantioselective Addition of Alcohols to Isatin-Derived Ketimines[J]. Tetrahedron, 2019,60(17):1161-1165. doi: 10.1016/j.tetlet.2019.03.049
Zhu J Y, Yang W L, Liu Y Z. Copper(Ⅰ)-catalyzed Asymmetric Mannich Reaction of Glycine Schiff Bases with Isatin-derived Ketimines:Enantioselective Synthesis of 3-Substituted 3-Aminooxindoles[J]. Org Chem Front, 2018,5(1):70-74.
Zhao B L, Du D M. Catalytic Asymmetric Mannich/Cyclization of 2-Isothiocyanato-1-indanones:An Approach to the Synthesis of Bispirocyclic Indanone-Thioimidazolidine-Oxindoles[J]. Org Lett, 2018,20(13):3797-3800. doi: 10.1021/acs.orglett.8b01389
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