Amino-indanol-catalyzed asymmetric michael additions of oxindoles to protected 2-amino-1-nitroethenes for the synthesis of 3,3′-disubstituted oxindoles bearing α,β-diamino functionality

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 4008-4017

  Liu, Xiong Li ^a,d   Wu, Zhi Jun ^b   Du, Xi Lin ^c   Zhang, Xiao Mei ^a   Yuan, Wei Cheng ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

^c FOURTH MILITARY MEDICAL UNIVERSITY   (China)

^d UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ASYMMETRIC INDUCTION; DIASTEREOSELECTIVITIES; HIGH YIELD; MICHAEL ADDITION REACTIONS; MICHAEL ADDITIONS; MICHAEL ADDUCTS; ORGANOCATALYTIC; OXINDOLES; POTENTIAL UTILITY; STEREOCENTERS;

ADDITION REACTIONS; BEARINGS (STRUCTURAL); CATALYSIS; ENANTIOSELECTIVITY;

SYNTHESIS (CHEMICAL);

3 (1 ACETAMIDO 2 NITROETHYL) 3 BENZYL 2 OXOINDOLIN 1 YLPROPIONATE; ETHYLENE; N [1 (3 BENZYL 2 OXO 1 PHENYLINDOLIN 3 YL) 2 NITROETHYL]ACETAMIDE; N [1 [3 (3 METHOXYBENZYL) 2 OXOINDOLIN 3 YL] 2 (4 METHYLPHENYLSULFONAMIDO)ETHYL]ACETAMIDE; OXINDOLE; TERT BUTYL 3 (1 ACETAMIDO 2 AMINOETHYL) 3 (3 METHOXYBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 2 OXO 3 (THIOPHEN 2 YLMETHYL)INDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 2 OXO 3 PROPYLINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (2 ETHOXY 2 OXOETHYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (2 FLUOROBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (2 METHOXYBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (3 METHOXYBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (3 METHYLBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (3,4 DIMETHOXYBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (3,5 DIMETHYLBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (3,5 DIMETHYLPHENYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (4 METHOXYBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (4 METHYLBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 (NAPHTHALEN 1 YLMETHYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 BENZYL 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 BENZYL 5 FLUORO 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 BENZYL 5 METHYL 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 ACETAMIDO 2 NITROETHYL) 3 BUTYL 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 (1 BENZAMIDO 2 NITROETHYL) 3 (3 METHYLBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; TERT BUTYL 3 [1 ACETAMIDO 2 (TERT BUTOXYCARBONYLAMINO)ETHYL] 3 (3 METHOXYBENZYL) 2 OXOINDOLINE 1 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; BIOTRANSFORMATION; CATALYST; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; MICHAEL ADDITION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

AMINES; CATALYSIS; INDANS; INDOLES; NITRO COMPOUNDS;

EID: 79956081247     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2004378     Document Type: Article

References (43)

1. For selected reviews, see: Hibino, S.; Choshi, T. Nat. Prod. Rep. 2001, 18, 66
2. Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36
3. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945
4. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
5. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748 For some selected examples, see: Zhang, X.; Smith, C. D. Mol. Pharmacol. 1996, 49, 228
6. Malinakova, H. C.; Liebeskind, L. S. Org. Lett. 2000, 2, 4083
7. Wearing, X. Z.; Cook, J. M. Org. Lett. 2002, 4, 4237
8. Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197
9. Abadi, A. H.; Abou-Seri, S. M.; Abdel-Rahman, D. E.; Klein, C.; Lozach, O.; Meijer, L. Eur. J. Med. Chem. 2006, 41, 296
10. Reisman, S. E.; Ready, J. M.; Weiss, M. M.; Hasuoka, A.; Hirata, M.; Tamaki, K.; Ovaska, T. V.; Smith, C. J.; Wood, J. L. J. Am. Chem. Soc. 2008, 130, 2087
11. Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y.-C. Org. Lett. 2008, 10, 3583
12. Cheng, L.; Liu, L.; Jia, H.; Wang, D.; Chen, Y.-J. J. Org. Chem. 2009, 74, 4650
13. He, R.; Ding, C.; Maruoka, K. Angew. Chem., Int. Ed. 2009, 48, 4559
14. Kato, Y.; Furutachi, M.; Chen, Z.; Mitsunuma, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 9168
15. Bui, T.; Syed, S.; Barbas, C. F., III J. Am. Chem. Soc. 2009, 131, 8758
16. He, R.; Shirakawa, S.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 16620
17. Li, X.; Zhang, B.; Xi, Z.-G.; Luo, S. Z.; Cheng, J.-P. Adv. Synth. Catal. 2010, 352, 416
18. Ding, M.; Zhou, F.; Qian, Z.-Q.; Zhou, J. Org. Biomol. Chem. 2010, 8, 2912
19. Larsen, T. O.; Frydenvang, K.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 1998, 61, 1154
20. Ariza, M. R.; Larsen, T. O.; Petersen, B. O.; Duus, J. O.; Christophersen, C.; Barrero, A. F. J. Nat. Prod. 2001, 64, 1590
21. Kuriyama, T.; Kakemoto, E.; Takahashi, N.; Imamura, K.; Oyama, K.; Suzuki, E.; Harimaya, K.; Yaguchi, T.; Ozoe, Y. J. Agric. Food Chem. 2004, 52, 3884
22. Larsen, T. O.; Petersen, B. O.; Duus, J. O.; Sorensen, D.; Frisvad, J. C.; Hansen, M. E. J. Nat. Prod. 2005, 68, 871
23. Barrow, C. J.; Sun, H. H. J. Nat. Prod. 1994, 57, 471
24. Cascieri, M. A.; Macleod, A. M.; Underwood, D.; Shiao, L.-L.; Ber, E.; Sadowski, S.; Yu, H.; Merchant, K. J.; Swain, C. J.; Strader, C. D.; Fong, T. M. J. Biol. Chem. 1994, 269, 6587
25. For the synthesis of protected 2-amino-1-nitroethenes, see: Zhu, S.; Yu, S.; Wang, Y.; Ma, D. Angew. Chem., Int. Ed. 2010, 49, 4656
26. Krówczy?ski, A.; Kozerski, L. Synthesis 1983, 489
27. For selected reviews of Michael addition reaction, see: Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171
28. Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Synthesis 2007, 1279
29. Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701
30. For a representative review concerning the catalytic asymmetric synthesis of oxindoles bearing a tetrasubstituted stereocenter at the C-3 position, see: Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381 For selected examples, see: Bravo, N.; Mon, I.; Companyó, X.; Alba, A.-N.; Moyano, A.; Rios, R. Tetrahedron Lett. 2009, 50, 6624
31. Galzerano, P.; Bencivenni, G.; Pesciaioli, F.; Mazzanti, A.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem.-Eur. J. 2009, 15, 7846
32. Li, X.; Xi, Z.-G.; Luo, S.; Cheng, J.-P. Org. Biomol. Chem. 2010, 8, 77
33. Pesciaioli, F.; Tian, X.; Bencivenni, G.; Bartoli, G.; Melchiorre, P. Synlett 2010, 1704
34. Zhu, Q.; Lu, Y. Angew. Chem., Int. Ed. 2010, 49, 7753
35. Li, X.; Luo, S.; Cheng, J.-P. Chem. - Eur. J. 2010, 16, 14290
36. Liao, Y.-H.; Zhang, H.; Wu, Z.-J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron: Asymmetry 2009, 20, 2397
37. Liao, Y.-H.; Chen, W.-B.; Wu, Z.-J.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Adv. Synth. Catal. 2010, 352, 827
38. Chen, W.-B.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron 2010, 66, 1441
39. Liao, Y.-H.; Liu, X.-L.; Wu, Z.-J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2010, 12, 2896
40. Chen, W.-B.; Wu, Z.-J.; Pei, Q.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2010, 12, 3132
41. Liu, X.-L.; Liao, Y.-H.; Wu, Z.-J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. J. Org. Chem. 2010, 75, 4872
42. Soh, J. Y.-T.; Tan, C.-H. J. Am. Chem. Soc. 2009, 131, 6904
43. The crystallographic coordinates have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 813793. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html.