Secondary-amine-catalyzed asymmetric Michael addition of N-tert-butoxycarbonyl-protected oxindoles to maleimides

Synthesis (Germany)

Volumn 44, Issue 16, 2012, Pages 2601-2606

  Yang, Xuena ^a   Wang, Chuan ^a   Ni, Qijian ^a   Enders, Dieter ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Bronsted base; heterocycles; Michael addition; organocatalysis; oxindole

Indexed keywords

BRONSTED BASE; HETEROCYCLES; MICHAEL ADDITIONS; ORGANOCATALYSIS; OXINDOLE;

CATALYSIS; ORGANIC COMPOUNDS; REACTION KINETICS;

ADDITION REACTIONS;

3 [3 BENZYL 2 OXO 2,3 DIHYDRO 1H INDOL 3 YL] 1 PHENYLPYRROLIDINE 2,5 DIONE; INDOLE DERIVATIVE; MALEIMIDE DERIVATIVE; N (TERT BUTOXYCARBONYL)OXINDOLE DERIVATIVE; OXINDOLE DERIVATIVE; TERT BUTYL 3 (1,3 BENZODIOXOL 5 YLMETHYL) 3 [2,5 DIOXO 1 PHENYLPYRROLIDIN 3 YL] 2 OXOINDOLINE 1 CARBOXYLIC ACID; TERT BUTYL 3 (2,5 DIOXOPYRROLIDIN 3 YL) 2 OXOINDOLINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [1 (4 BROMOPHENYL) 2,5 DIOXOPHENYLPYRROLIDIN 3 YL] 2 OXOINDOLINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [1 (4 BROMOPHENYL) 2,5 DIOXOPHENYLPYRROLIDIN 3 YL] 3 METHYL 2 OXOINDOLINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [2,5 DIOXO 1 PHENYLPYRROLIDIN 3 YL] 3 (3 FLUOROBENZYL) 2 OXOINDOLINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [2,5 DIOXO 1 PHENYLPYRROLIDIN 3 YL] 3 (4 METHOXYBENZYL) 2 OXOINDOLINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [2,5 DIOXO 1 PHENYLPYRROLIDIN 3 YL] 3 (4 METHYLBENZYL) 2 OXOINDOLINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [2,5 DIOXO 1 PHENYLPYRROLIDIN 3 YL] 3 METHYL 2 OXOINDOLINE 1 CARBOXYLIC ACID; TERT BUTYL 3 BENZYL 3 [1 (4 BROMOPHENYL) 2,5 DIOXOPHENYLPYRROLIDIN 3 YL] 2 OXOINDOLINE 1 CARBOXYLIC ACID; TERT BUTYL 3 BENZYL 3 [2,5 DIOXO 1 PHENYLPYRROLIDIN 3 YL] 2 OXOINDOLINE 1 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; MICHAEL ADDITION;

EID: 84864866220     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316577     Document Type: Article

References (89)

1. Mehta RG, Liu J, Constantinou A, Hawthorne M, Pezzuto JM, Moon RC, Moriarty RM. Anticancer Res.: 1994; 14 1209
2. 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
3. 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
4. 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
5. Dandia A, Sati M, Arya K, Sharma R, Loupy A. Chem. Pharm. Bull.: 2003; 51 1137
6. Serradeil-Le Gal C, Derick S, Brossard G, Manning M, Simiand J, Gaillard R, Griebel G, Guillon G. Stress: 2003; 6 199
7. Neel DA, Brown ML, Lander PA, Grese TA, Defauw JM, Doti RA, Fields T, Kelly SA, Smith S, Zimmerman KM, Steinberg MI, Jadhav PK. Bioorg. Med. Chem. Lett.: 2005; 15 2553
8. Bernard K, Bogliolo S, Ehrenfeld J. Br. J. Pharmacol.: 2005; 144 1037
9. Luk K.-C, So S.-S, Zhang J, Zhang Z. WO 2006136606: 2006
10. Ding K, Lu Y, Nikolovska-Coleska Z, Wang G, Qiu S, Shangary S, Gao W, Qin D, Stuckey J, Krajewski K, Roller PP, Wang S. J. Med. Chem.: 2006; 49 3432
11. Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Wu TY.-H, He Y. Bioorg. Med. Chem. Lett.: 2006; 16 2105
12. Pedras MS. C, Hossain M. Org. Biomol. Chem.: 2006; 4 2581
13. Uddin MK, Reignier SG, Coulter T, Montalbetti C, Grånäs C, Butcher S, Krog-Jensen C, Felding J. Bioorg. Med. Chem. Lett.: 2007; 17 2854
14. Kawasaki T, Ogawa A, Takashima Y, Sakamoto M. Tetrahedron Lett.: 2003; 44 1591
15. Huang A, Kodanko JJ, Overman LE. J. Am. Chem. Soc.: 2004; 126 14043
16. Kitajima M, Mori I, Arai K, Kogure N, Takayama H. Tetrahedron Lett.: 2006; 47 3199
17. Trost BM, Zhang Y. J. Am. Chem. Soc.: 2006; 128 4590
18. Bui T, Syed S, Barbas CF III. J. Am. Chem. Soc.: 2009; 131 8758
19. Guo C, Song J, Huang J.-Z, Chen P.-H, Luo S.-W, Gong L.-Z. Angew. Chem. Int. Ed.: 2012; 51 1046
20. Marti C, Carreira EM. Eur. J. Org. Chem.: 2003; 2209
21. Galliford CV, Scheidt KA. Angew. Chem. Int. Ed.: 2007; 46 8748
22. Trost BM, Brennan MK. Synthesis: 2009; 3003
23. Zhou F, Liu J.-L, Zhou J. Adv. Synth. Catal.: 2010; 352 1381
24. Kato Y, Furutachi M, Chen Z, Mitsunuma H, Matsunaga S, Shibasaki M. J. Am. Chem. Soc.: 2009; 131 9168
25. He R, Shirakawa S, Maruoka K. J. Am. Chem. Soc.: 2009; 131 16620
26. He R, Ding C, Maruoka K. Angew. Chem. Int. Ed.: 2009; 48 4559
27. Galzerano P, Bencivenni G, Pesciaioli F, Mazzanti A, Giannichi B, Sambri L, Bartoli G, Melchiorre P. Chem.-Eur. J.: 2009; 15 7846
28. Bravo N, Mon I, Companyó X, Alba A.-N, Moyano A, Rios R. Tetrahedron Lett.: 2009; 50 6624
29. Zhu Q, Lu Y. Angew. Chem. Int. Ed.: 2010; 49 7753
30. Liao Y.-H, Liu X.-L, Wu Z.-J, Cun L.-F, Zhang X.-M, Yuan W.-C. Org. Lett.: 2010; 12 2896
31. Li X, Luo S, Cheng J.-P. Chem.-Eur. J.: 2010; 16 14290
32. Sun W, Hong L, Liu C, Wang R. Tetrahedron: Asymmetry: 2010; 21 2493
33. Ding M, Zhou F, Liu Y.-L, Wang C.-H, Zhao X.-L, Zhou J. Chem. Sci.: 2011; 2 2035
34. Freund MH, Tsogoeva SB. Synlett: 2011; 503
35. Zheng W, Zhang Z, Kaplan MJ, Antilla JC. J. Am. Chem. Soc.: 2011; 133 3339
36. Duan S.-W, An J, Chen J.-R, Xiao W.-J. Org. Lett.: 2011; 13 2290
37. Tan B, Candeias NR, Barbas CF III. Nat. Chem.: 2011; 3 473
38. Zhang T, Cheng L, Hameed S, Liu L, Wang D, Chen Y.-J. Chem. Commun.: 2011; 47 6644
39. Bergonzini G, Melchiorre P. Angew. Chem. Int. Ed.: 2012; 51 971
40. Wang C, Yang X, Enders D. Chem.-Eur. J.: 2012; 18 4832
41. Retini M, Bergonzini G, Melchiorre P. Chem. Commun.: 2012; 48 3336
42. Li L, Chen W, Yang W, Pan Y, Liu H, Tan C.-H, Jiang Z. Chem. Commun.: 2012; 48 5124
43. Bartoli G, Bosco M, Carlone A, Cavalli A, Locatelli M, Mazzanti A, Ricci P, Sambri L, Melchiorre P. Angew. Chem. Int. Ed.: 2006; 45 4966
44. Shen J, Nguyen TT, Goh Y.-P, Ye W, Fu X, Xu J, Tan C.-H. J. Am. Chem. Soc.: 2006; 128 13692
45. Zhao G.-L, Xu Y, Sundén H, Eriksson L, Sayah M, Córdova A. Chem. Commun.: 2007; 43 734
46. Zhu L, Xie H, Li H, Wang J, Jiang W, Wang W. Adv. Synth. Catal.: 2007; 349 1882
47. Lu J, Zhou W.-J, Liu F, Loh T.-P. Adv. Synth. Catal.: 2008; 350 1796
48. Gioia C, Hauville A, Bernardi L, Fini F, Ricci A. Angew. Chem. Int. Ed.: 2008; 47 9236
49. Soh JY.-T, Tan C.-H. J. Am. Chem. Soc.: 2009; 131 6904
50. Jiang Z, Pan Y, Zhao Y, Ma T, Lee R, Yang Y, Huang K.-W, Wong MW, Tan C.-H. Angew. Chem. Int. Ed.: 2009; 48 3627
51. Xue F, Liu L, Zhang S, Duan W, Wang W. Chem.-Eur. J.: 2010; 16 7979
52. Alba A.-NR, Valero G, Calbet T, Font-Bardía M, Moyano A, Rios R. Chem.-Eur. J.: 2010; 16 9884
53. Yu F, Sun X, Jin Z, Wen S, Liang X, Ye J. Chem. Commun. (Cambridge): 2010; 46 4589
54. Yu F, Yin Z, Huang H, Ye T, Liang X, Ye J. Org. Biomol. Chem.: 2010; 8 4767
55. Gómez-Torres E, Alonso DA, Gómez-Bengoa E, Nájera C. Org. Lett.: 2011; 13 6106
56. Mazzanti A, Calbet T, Font-Bardia M, Moyano A, Rios R. Org. Biomol. Chem.: 2012; 10 1645
57. Berkessel A, Gröger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis. Wiley-VCH Weinheim: 2005
58. Enantioselective Organocatalysis: Reactions and Experimental Procedures. Dalko PI. Wiley-VCH Weinheim: 2007
59. Special issue on Organocatalysis: Chem. Rev.: 2007; 107 5413
60. Pellissier H. Tetrahedron: 2007; 63 9267
61. Marcia de Figueiredo R, Christmann M. Eur. J. Org. Chem.: 2007; 2575
62. Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed.: 2007; 46 1570
63. Dondoni A, Massi A. Angew. Chem. Int. Ed.: 2008; 47 4638
64. Enders D, Narine AA. J. Org. Chem.: 2008; 73 7857
65. Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew. Chem. Int. Ed.: 2008; 47 6138
66. Bertelsen S, Jorgensen KA. Chem. Soc. Rev.: 2009; 38 2178
67. Bella M, Gasperi T. Synthesis: 2009; 1583
68. Grondal C, Jeanty M, Enders D. Nat. Chem.: 2010; 2 167
69. Merino P, Marqués-Lopéz E, Tejero T, Herrera RP. Synthesis: 2010; 1
70. Terada M. Synthesis: 2010; 1929
71. Albrecht, Jiang H, Jorgensen KA. Angew. Chem. Int. Ed.: 2011; 50 8492
72. Pellissier H. Tetrahedron: 2012; 68 2197
73. Giacalone F, Gruttadauria M, Agrigento P, Noto R. Chem. Soc. Rev.: 2012; 41 2406
74. Pellissier H. Adv. Synth. Catal.: 2012; 354 237
75. Beeson TD, Mastracchio A, Hong J.-B, Ashton K, MacMillan DW. C. Science: 2007; 316 582
76. Sibi MP, Hasegawa M. J. Am. Chem. Soc.: 2007; 129 4124
77. Jang H.-Y, Hong J.-BMacMillan D. W. C. J. Am. Chem. Soc.: 2007; 129 7004
78. Juli NT, Lee EC. Y, MacMillan DW. C. J. Am. Chem. Soc.: 2010; 132 10015
79. Neumann M, Füldner S, König B, Zeitler K. Angew. Chem. Int. Ed.: 2011; 50 951
80. Russo A, Lattanzi A. Adv. Synth. Catal.: 2008; 350 1991
81. Zheng C, Li Y, Yang Y, Wang H, Cui H, Zhang J, Zhao G. Adv. Synth. Catal.: 2009; 351 1685
82. Palumbo C, Mazzeo G, Mazziotta A, Gambacorta A, Loreto MA, Migliorini A, Superchi S, Tofani D, Gasperi T. Org. Lett.: 2011; 13 6248
83. Fang L, Lin A, Hu H, Zhu C. Chem.-Eur. J.: 2009; 15 7039
84. Lin A, Fang L, Zhu X, Zhu C, Cheng Y. Adv. Synth. Catal.: 2011; 353 545
85. Lattanzi A. Tetrahedron: Asymmetry: 2006; 17 837
86. Russo A, Lattanzi A. Tetrahedron: Asymmetry: 2010; 21 1155
87. Russo A, Capobianco A, Perfetto A, Lattanzi A, Peluso A. Eur. J. Org. Chem.: 2011; 1922
88. Russo A, Meninno S, Tedesco C, Lattanzi A. Eur. J. Org. Chem.: 2011; 5096
89. Lattanzi A, De Fusco C, Russo A, Poater A, Cavallo L. Chem. Commun.: 2012; 48 1650