Synthesis, Table of Contents Synthesis 2017; 49(22): 4986-4995DOI: 10.1055/s-0036-1590823 paper © Georg Thieme Verlag Stuttgart · New York Organocatalytic Asymmetric Synthesis of 2,3′-Connected Bis-Indolinones by Mannich Reactions of N-Acetylindolin-3-ones with Isatin N-Boc Ketimines V. Pratap Reddy Gajulapalli a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany , Ehsan Jafari a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany , Dipti S. Kundu a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany , Suruchi Mahajan a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany , Anssi Peuronen b Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland Email: enders@rwth-aachen.de , Kari Rissanen b Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland Email: enders@rwth-aachen.de , Dieter Enders* a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany › Author Affiliations Recommend Article Abstract Buy Article All articles of this category 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 Key wordsasymmetric synthesis - indolinone - bifunctional thiourea - organocatalysis - Mannich reaction Full Text References 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 Supplementary Material Supplementary Material Supporting Information