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Synthesis 2017; 49(22): 4986-4995
DOI: 10.1055/s-0036-1590823
DOI: 10.1055/s-0036-1590823
paper
Organocatalytic Asymmetric Synthesis of 2,3′-Connected Bis-Indolinones by Mannich Reactions of N-Acetylindolin-3-ones with Isatin N-Boc Ketimines
Further Information
Publication History
Received: 02 June 2017
Accepted: 06 June 2017
Publication Date:
01 August 2017 (online)
Abstract
A highly diastereo- and enantioselective Mannich reaction of N-acetylindolin-3-ones with isatin N-Boc ketimines to form 2,3′-connected bis-indolinones is developed employing a low loading of a readily available bifunctional thiourea catalyst. The asymmetric synthesis connects two indolinones via a vic-diamine unit and generates two neighboring stereocenters.
Key words
asymmetric synthesis - indolinone - bifunctional thiourea - organocatalysis - Mannich reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590823 .
- Supporting Information
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References
- 1 Lim K.-H. Kam T.-S. Helv. Chim. Acta 2007; 90: 31
- 2 Hayashi H. Takiuchi K. Murao S. Arai M. Agric. Biol. Chem. 1988; 52: 2131
- 3 Kam T.-S. Subramaniam G. Lim K.-H. Choo Y.-M. Tetrahedron Lett. 2004; 45: 5995
- 4 Nge C.-E. Gan C.-Y. Lim K.-H. Ting K.-N. Low Y.-Y. Kam T.-S. Org. Lett. 2014; 16: 6330
- 5 Kim J. Schneekloth JS. Sorensen E. J. Chem. Sci. 2012; 3: 2849
- 6 Phillipson JD. Supavita N. Phytochemistry 1983; 22: 180
- 7a de Graaff C. Ruijter E. Orru RV. A. Chem. Soc. Rev. 2012; 41: 3969
- 7b Karimi B. Enders D. Jafari E. Synthesis 2013; 45: 2769
- 8a Arend M. Westermann B. Risch N. Angew. Chem. Int. Ed. 1998; 37: 1044
- 8b Cordova A. Acc. Chem. Res. 2004; 37: 102
- 9a Yan W. Wang D. Feng J. Li P. Zhao D. Wang R. Org. Lett. 2012; 14: 2512
- 9b Hara N. Nakamura S. Sano M. Tamura R. Funahashi Y. Shibata N. Chem. Eur. J. 2012; 18: 9276
- 9c Lv H. Tiwari B. Mo J. Xing C. Chi YR. Org. Lett. 2012; 14: 5412
- 9d Nakamura S. Hyodo K. Nakamura M. Nakane D. Masuda H. Chem. Eur. J. 2013; 19: 7304
- 9e Chen X. Chen H. Ji X. Jiang H. Yao J. Liu H. Org. Lett. 2013; 15: 1846
- 9f Liu Y.-L. Zhou J. Chem. Commun. 2013; 49: 4421
- 9g Wang D. Liang J. Feng J. Wang K. Sun Q. Zhao L. Li D. Yan W. Wang R. Adv. Synth. Catal. 2013; 355: 548
- 9h Tang Z. Shi Y. Mao H. Zhu X. Li W. Cheng Y. Zheng W.-H. Zhu C. Org. Biomol. Chem. 2014; 12: 6085
- 9i Beceño C. Chauhan P. Rembiak A. Wang A. Enders D. Adv. Synth. Catal. 2015; 357: 672
- 9j Zhao K. Shu T. Jia J. Raabe G. Enders D. Chem. Eur. J. 2015; 21: 3933
- 9k Zhu Y. Zhang E. Luo C. Li X. Cheng J.-P. Tetrahedron 2015; 71: 4090
- 9l Yi Z. Yao L. Qingbin M. Xin L. Org. Chem. Front. 2016; 3: 709
- 9m Zhao K. Zhi Y. Li X. Puttreddy R. Rissanen K. Enders D. Chem. Commun. 2016; 52: 2249
- 9n Montesinos-Magraner M. Vila C. Canton R. Blay G. Fernández I. Muñoz MC. Pedro JR. Angew. Chem. Int. Ed. 2015; 54: 6320
- 9o Sankar MG. Garcia-Castro M. Golz C. Strohmann C. Kumar K. Angew. Chem. Int. Ed. 2016; 55: 9709
- 9p Cheng P. Guo W. Chen P. Liu Y. Du X. Li C. Chem. Commun. 2016; 52: 3418
- 9q Zhou L.-J. Zhang Y.-C. Jiang F. He G. Yan J. Lu H. Zhang S. Shi F. Adv. Synth. Catal. 2016; 358: 3069
- 9r Cheng C. Lu X. Ge L. Chen J. Cao W. Wu X. Zhao G. Org. Chem. Front. 2017; 4: 101
- 10a Chauhan P. Chimni SS. Tetrahedron: Asymmetry 2013; 24: 343
- 10b Kaur J. Chimni SS. Mahajan S. Kumar A. RSC Adv. 2015; 5: 52481
- 11a Liu Y.-Z. Cheng R.-L. Xu P.-F. J. Org. Chem. 2011; 76: 2884
- 11b Sun W.-S. Hong L. Wang R. Chem. Eur. J. 2011; 17: 6030
- 11c Liu Y.-Z. Zhang J. Xu P.-F. Luo Y.-C. J. Org. Chem. 2011; 76: 7551
- 11d Jin C.-Y. Wang Y. Liu Y.-Z. Shen C. Xu P.-F. J. Org. Chem. 2012; 77: 11307
- 11e Lu Y. Tang W. Zhang Y. Du D. Lu T. Adv. Synth. Catal. 2013; 355: 321
- 11f Ni Q. Song X. Raabe G. Enders D. Chem. Asian J. 2014; 9: 1535
- 11g Zhao Y.-L. Wang Y. Cao J. Liang Y.-M. Xu P.-F. Org. Lett. 2014; 16: 2438
- 11h Mahajan S. Chauhan P. Loh CC. J. Uzungelis S. Raabe G. Enders D. Synthesis 2015; 47: 1024
- 11i Chen S. Wang Y. Zhou Z. J. Org. Chem. 2016; 81: 11432
- 12 CCDC 1543566 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 13 Yan W. Wang D. Feng J. Li P. Zhao D. Wang R. Org. Lett. 2012; 14: 2512
- 14 Matsumoto S. Samata D. Akazome M. Ogura K. Tetrahedron Lett. 2009; 50: 111
- 15 Kawasaki T. Nonaka Y. Uemura M. Sakamoto M. Synthesis 1991; 701