Catalytic asymmetric synthesis of 3-hydroxyl-2-oxindoles via enantioselective Morita-Baylis-Hillman reaction of isatins

Tetrahedron

Volumn 67, Issue 16, 2011, Pages 2974-2978

  Wang, Ci Ci ^a   Wu, Xin Yan ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

3 Hydroxyl 2 oxindole; Bifunctional phosphinothiourea; Enantioselective organocatalysis; Isatin; Morita Baylis Hillman reaction

Indexed keywords

3 HYDROXYL 2 OXINDOLE DERIVATIVE; ACRYLIC ACID; CYCLOHEXANE; ISATIN DERIVATIVE; OXINDOLE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 79953167128     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.02.045     Document Type: Article

References (62)

1. For reviews, see:
2. S. Hibino, and T. Choshi Nat. Prod. Rep. 18 2001 66 87
3. H. Lin, and S.J. Danishefsky Angew. Chem., Int. Ed. 42 2003 36 51
4. C. Marti, and E.M. Carreira Eur. J. Org. Chem. 2003 2209 2219
5. C.V. Galliford, and K.A. Scheidt Angew. Chem., Int. Ed. 46 2007 8748 8758
6. S. Peddibhotla Curr. Bioact. Compd. 5 2009 20 38
7. For reviews, see:
8. A.B. Dounay, and L.E. Overman Chem. Rev. 103 2003 2945 2963
9. F. Zhou, Y.-L. Liu, and J. Zhou Adv. Synth. Catal. 352 2010 1381 1407
10. R. Shintani, M. Inoue, and T. Hayashi Angew. Chem., Int. Ed. 45 2006 3353 3356
11. M. Kitajima, I. Mori, K. Arai, N. Kogure, and H. Takayama Tetrahedron Lett. 47 2006 3199 3202
12. P.Y. Toullec, R.B.C. Jagt, J.G. de Vries, B.L. Feringa, and A.J. Minnaard Org. Lett. 8 2006 2715 2718
13. D. Tomita, K. Yamatsugu, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 131 2009 6946 6948
14. J. Itoh, S.B. Han, and M.J. Krische Angew. Chem., Int. Ed. 48 2009 6313 6316
15. H. Lai, Z. Huang, Q. Wu, and Y. Qin J. Org. Chem. 74 2009 283 288
16. X.-C. Qiao, S.-F. Zhu, and Q.-L. Zhou Tetrahedron: Asymmetry 20 2009 1254 1261
17. V. Hanhan, A.H. Sahin, T.W. Chang, J.C. Fettinger, and A.K. Franz Angew. Chem., Int. Ed. 49 2010 744 747
18. For recent reviews on asymmetric organocatalysis, see:
19. P.I. Dalko Enantioselective Organocatalysis: Reactions and Experimental Procedures 2007 Wiley-VCH Weinheim
20. B. List Asymmetric Organocatalysis 2010 Springer Heidelberg
21. H. Pellissier Tetrahedron 63 2007 9267 9331
22. M.J. Gaunt, C.C.C. Johansson, A. McNally, and N.T. Vo Drug Discovery Today 12 2007 8 27
23. A. Dondoni, and A. Massi Angew. Chem., Int. Ed. 47 2008 4638 4660
24. D.W.C. MacMillan Nature 455 2008 304 308
25. S. Bertelsen, and K.A. Jøgensen Chem. Soc. Rev. 38 2009 2178 2189
26. G. Luppi, P.G. Cozzi, M. Monari, B. Kaptein, Q.B. Broxterman, and C. Tomasini J. Org. Chem. 70 2005 7418 7421
27. J.-R. Chen, X.-P. Liu, X.-Y. Zhu, L. Li, T.-F. Qian, J.-M. Zhang, and W.-J. Xiao Tetrahedron 63 2007 10437 10444
28. S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, and T. Toru Chem. - Eur. J. 14 2008 8079 8081
29. G. Luppi, M. Monari, R.J. CorrTa, F.A. Violante, A.C. Pinto, B. Kaptein, Q.B. Broxterman, S.J. Garden, and C. Tomasini Tetrahedron 62 2006 12017 12024
30. V. Malkov, M.A. Kabeshov, M. Bella, O. Kysilka, D.A. Malyshev, K. Pluhčkov, and P. Kočovský Org. Lett. 9 2007 5473 5476
31. G. Angelici, R.J. Corrêa, S.J. Garden, and C. Tomasini Tetrahedron Lett. 50 2009 814 817
32. N. Hara, S. Nakamura, N. Shibata, and T. Toru Chem. - Eur. J. 15 2009 6790 6793
33. T. Itoh, H. Ishikawa, and Y. Hayashi Org. Lett. 11 2009 3854 3857
34. F. Xue, S. Zhang, L. Liu, W. Duan, and W. Wang Chem. - Asian J. 4 2009 1664 1667
35. J. Deng, S. Zhang, P. Ding, H. Jiang, W. Wang, and J. Li Adv. Synth. Catal. 352 2010 833 838
36. M. Raj, N. Veerasamy, and V.K. Singh Tetrahedron Lett. 51 2010 2157 2159
37. For reviews on the asymmetric MBH reactions, see:
38. G. Masson, C. Housseman, and J. Zhu Angew. Chem., Int. Ed. 46 2007 4614 4628
39. D. Basavaiah, K.V. Rao, and R.J. Reddy Chem. Soc. Rev. 36 2007 1581 1588
40. P.R. Krishna, R. Sachwani, and P.S. Reddy Synlett 2008 2897 2912
41. V. Carrasco-Sanchez, M.J. Simirgiotis, and L.S. Santos Molecules 14 2009 3989 4021
42. Y. Wei, and M. Shi Acc. Chem. Res. 43 2010 1005 1018
43. S.J. Garden, and J.M.S. Skakle Tetrahedron Lett. 43 2002 1969 1972
44. Y.M. Chung, Y.J. Im, and J.N. Kim Bull. Korean Chem. Soc. 23 2002 1651 1655
45. S.Z. Luo, X.L. Mi, P.G. Wang, and J.-P. Cheng J. Org. Chem. 69 2004 8413 8422
46. D. Basavaiah, S. Roy, and U. Das Tetrahedron 66 2010 5612 5622
47. Selected papers for the application of MBH adducts of isatins in the synthesis of oxindole derivatives:
48. S.C. Kim, S. Gowrisankar, and J.N. Kim Tetrahedron Lett. 47 2006 3463 3466
49. P. Shanmugam, B. Viswambharan, and S. Madhavan Org. Lett. 9 2007 4095 4098
50. After the submission of this manuscript, the enantioselective MBH reaction of isatin was reported.
51. Y.-L. Liu, B.-L. Wang, J.-J. Cao, L. Chen, Y.-X. Zhang, C. Wang, and J. Zhou J. Am. Chem. Soc. 132 2010 15176 15178
52. X.-Y. Guan, Y. Wei, and M. Shi Chem. - Eur. J. 16 2010 13617 13621
53. F. Zhong, G.-Y. Chen, and Y. Lu Org. Lett. 13 2011 82 85
54. K. Yuan, L. Zhang, H.-L. Song, Y. Hu, and X.-Y. Wu Tetrahedron Lett. 49 2008 6262 6264
55. K. Yuan, H.-L. Song, Y. Hu, and X.-Y. Wu Tetrahedron 65 2009 8185 8190
56. J.-J. Gong, K. Yuan, and X.-Y. Wu Tetrahedron: Asymmetry 20 2009 2117 2120
57. J.-J. Gong, K. Yuan, H.-L. Song, and X.-Y. Wu Tetrahedron 66 2010 2439 2443
58. K. Yuan, H.-L. Song, Y. Hu, J.-F. Fang, and X.-Y. Wu Tetrahedron: Asymmetry 21 2010 903 908
59. J. Vesely, P. Dziedzic, and A. Cordova Tetrahedron Lett. 48 2007 6900 6904
60. P. Shanmugam, V. Vaithiyanathan, and B. Viswambharan Tetrahedron Lett. 47 2006 6851 6855
61. P. Shanmugam, and V. Vaithiyanathan Tetrahedron 64 2008 3322 3330
62. P. Shanmugam, V. Vaithiyanathan, and K. Selvakumar Tetrahedron Lett. 49 2008 2119 2123