Synthesis, Table of Contents Synthesis 2017; 49(22): 4986-4995DOI: 10.1055/s-0036-1590823 paper © Georg Thieme Verlag Stuttgart · New YorkOrganocatalytic Asymmetric Synthesis of 2,3′-Connected Bis-Indolinones by Mannich Reactions of N-Acetylindolin-3-ones with Isatin N-Boc Ketimines Authors Author Affiliations 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 Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) 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. 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