Synthesis, Table of Contents Synthesis 2012; 44(16): 2601-2606DOI: 10.1055/s-0032-1316577 paper © Georg Thieme Verlag Stuttgart · New YorkSecondary-Amine-Catalyzed Asymmetric Michael Addition of N-tert-Butoxycarbonyl-Protected Oxindoles to Maleimides Xuena Yang Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127 Email: enders@rwth-aachen.de , Chuan Wang Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127 Email: enders@rwth-aachen.de , Qijian Ni Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127 Email: enders@rwth-aachen.de , Dieter Enders* Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127 Email: enders@rwth-aachen.de› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract A secondary-amine-catalyzed asymmetric Michael addition of 3-substituted N-(tert-butoxycarbonyl)oxindoles to maleimides with activation by a Brønsted base gives the corresponding products in high yields (86–98%), excellent diastereomeric ratios (dr > 99:1), and high enantiomeric excesses (86–91% ee). Key words Key wordsBrønsted base - Michael addition - heterocycles - organocatalysis - oxindole Full Text References References 1a Mehta RG, Liu J, Constantinou A, Hawthorne M, Pezzuto JM, Moon RC, Moriarty RM. Anticancer Res. 1994; 14: 1209 1b Tokunaga T, Hume WE, Umezome T, Okazaki K, Ueki Y, Kumagai K, Hourai S, Nagamine J, Seki H, Taiji M, Noguchi H, Nagata R. J. Med. Chem. 2001; 44: 4641 1c Hewawasam P, Erway M, Moon SL, Knipe J, Weiner H, Boissard CG, Post-Munson DJ, Gao Q, Huang S, Gribkoff VK, Meanwell NA. J. Med. Chem. 2002; 45: 1487 1d Hewawasam P, Gribkoff VK, Pendri Y, Dworetzky SI, Meanwell NA, Martinez E, Boissard CG, Post-Munson DJ, Trojnacki JT, Yeleswaram K, Pajor LM, Knipe J, Gao Q, Perrone R, Starrett JE. Jr. Bioorg. Med. Chem. Lett. 2002; 12: 1023 1e Dandia A, Sati M, Arya K, Sharma R, Loupy A. Chem. Pharm. Bull. 2003; 51: 1137 1f Serradeil-Le Gal C, Derick S, Brossard G, Manning M, Simiand J, Gaillard R, Griebel G, Guillon G. 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