Phosphine-catalyzed asymmetric [4+1] annulation of activated α,β-unsaturated ketones with Morita–Baylis–Hillman carbonates: enantioselective synthesis of spirooxindoles containing two adjacent quaternary stereocenters

Chemical Communications

Volumn 50, Issue 64, 2014, Pages 8912-8914

  Hu, Fang Le ^a   Wei, Yin ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID DERIVATIVE; KETONE DERIVATIVE; OXINDOLE; PHOSPHINE;

ARTICLE; BAYLIS HILLMAN REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOSELECTIVITY; NUCLEOPHILICITY; SOLVENT EFFECT; STEREOSPECIFICITY; SYNTHESIS; X RAY DIFFRACTION;

EID: 84904438396     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc03479a     Document Type: Article

References (72)

1. S. E. Denmark, G. L. Beutner, Angew. Chem., Int. Ed., 2008, 47, 1560
2. X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res., 2001, 34, 535
3. J. L. Methot, W. R. Roush, Adv. Synth. Catal., 2004, 346, 1035
4. A. Marinetti, A. Voituriez, Synlett, 2010, 174
5. S. Xu, Z. He, Sci. Sin.: Chim., 2010, 40, 856
6. Z.-M. Wang, X.-Z. Xu, O. Kwon, Chem. Soc. Rev., 2014, 43, 2927
7. L.-W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev., 2008, 37, 1140
8. B. J. Cowen, S. J. Miller, Chem. Soc. Rev., 2009, 38, 3102
9. Y. C. Fan, O. Kwon, Chem. Commun., 2013, 49, 11588
10. Y. Du, X. Lu, C. Zhang, Angew. Chem., Int. Ed., 2003, 42, 1035
11. Y. Du, J. Feng, X. Lu, Org. Lett., 2005, 7, 1987
12. J. Feng, X. Lu, A. Kong, X. Han, Tetrahedron, 2007, 63, 6035
13. S. Zheng, X. Lu, Org. Lett., 2008, 10, 4481
14. S. Zheng, X. Lu, Tetrahedron Lett., 2009, 50, 4532
15. S. Zheng, X. Lu, Org. Lett., 2009, 11, 3978
16. C.-W. Cho, J.-R. Kong, M. J. Krische, Org. Lett., 2004, 6, 1337
17. C.-W. Cho, M. J. Krische, Angew. Chem., Int. Ed., 2004, 43, 6689
18. B. M. Trost, R. M. Machacek, H. C. Tsui, J. Am. Chem. Soc., 2005, 127, 7014
19. Y.-S. Du, X.-L. Han, X.-Y. Lu, Tetrahedron Lett., 2004, 45, 4967
20. D. J. V. C. van Steenis, T. Marcelli, M. Lutz, A. L. Spek, J. H. van Maarseveen, H. Hiemstra, Adv. Synth. Catal., 2007, 349, 281
21. Y.-Q. Jiang, Y.-L. Shi, M. Shi, J. Am. Chem. Soc., 2008, 130, 7202
22. H.-L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, Y.-C. Chen, Angew. Chem., Int. Ed., 2009, 48, 5737
23. J. Peng, X. Huang, H.-L. Cui, Y.-C. Chen, Org. Lett., 2010, 12, 4260
24. T. Furukawa, T. Nishimine, E. Tokunaga, K. Hasegawa, M. Shiro, N. Shibata, Org. Lett., 2011, 13, 3972
25. T. Furukawa, J. Kawazoe, W. Zhang, T. Nishimine, E. Tokunaga, T. Matsumoto, M. Shiro, N. Shibata, Angew. Chem., Int. Ed., 2011, 50, 9684
26. F. Zhong, J. Luo, G. Y. Chen, X. Dou, Y. Lu, J. Am. Chem. Soc., 2012, 134, 10222
27. G.-Y. Chen, F. Zhong, Y. Lu, Org. Lett., 2012, 14, 3955
28. B. Wang, X. Companyó, J. Li, A. Moyano, R. Rios, Tetrahedron Lett., 2012, 53, 4124
29. R. Zhou, J.-F. Wang, H.-B. Song, Z.-J. He, Org. Lett., 2011, 13, 580
30. B. Tan, N. R. Candeias, C. F. Barbas III, J. Am. Chem. Soc., 2011, 133, 4672
31. F.-R. Zhong, X.-Y. Han, Y.-Q. Wang, Y.-X. Lu, Angew. Chem., Int. Ed., 2011, 50, 7837
32. Q.-G. Wang, S.-F. Zhu, L.-W. Ye, C.-Y. Zhou, X.-L. Sun, Y. Tang, Q.-L. Zhou, Adv. Synth. Catal., 2010, 352, 1914
33. Y. Wang, L. Liu, T. Zhang, N.-J. Zhong, D. Wang, Y.-J. Chen, J. Org. Chem., 2012, 77, 4143
34. F.-R. Zhong, G.-Y. Chen, X.-Y. Han, W.-J. Yao, Y.-X. Lu, Org. Lett., 2012, 14, 3764
35. J. Peng, X. Huang, L. Jiang, H.-L. Cui, Y.-C. Chen, Org. Lett., 2011, 13, 4584
36. N.-J. Zhong, F. Wei, Q.-Q. Xuan, L. Liu, D. Wang, Y.-J. Chen, Chem. Commun., 2013, 49, 11071
37. Z.-L. Chen, J.-L. Zhang, Chem. - Asian J., 2010, 5, 1542
38. P.-Z. Xie, Y. Huang, R.-Y. Chen, Org. Lett., 2010, 12, 3768
39. J.-J. Tian, R. Zhou, H.-B. Song, Z.-J. He, J. Org. Chem., 2011, 76, 2374
40. P.-Z. Xie, E.-Q. Li, J. Zheng, X. Li, Y. Huang, R.-Y. Chen, Adv. Synth. Catal., 2013, 355, 161-169
41. W. Yuan, H.-F. Zheng, Z.-H. Yu, Z.-L. Tang, D.-Q. Shi, Eur. J. Org. Chem., 2014, 583-591
42. H.-P. Deng, Y. Wei, M. Shi, Org. Lett., 2011, 13, 3348
43. H.-P. Deng, Y. Wei, M. Shi, Adv. Synth. Catal., 2012, 354, 783
44. H.-P. Deng, D. Wang, Y. Wei, M. Shi, Beilstein J. Org. Chem., 2012, 8, 1098
45. F.-L. Hu, Y. Wei, M. Shi, Tetrahedron, 2012, 68, 7911
46. X.-N. Zhang, H.-P. Deng, L. Huang, Y. Wei, M. Shi, Chem. Commun., 2012, 48, 8664
47. X.-Y. Han, W.-J. Yao, T.-L. Wang, Y.-R. Tan, Z.-Y. Yan, J. Kwiatkowski, Y.-X. Lu, Angew. Chem., Int. Ed., 2014, 53, 5643-5647
48. H. Lin, S. J. Danishefsky, Angew. Chem., Int. Ed., 2003, 42, 36
49. M. M.-C. Lo, C. S. Neumann, S. Nagayama, E. O. Perlstein, S. L. Schreiber, J. Am. Chem. Soc., 2004, 126, 16077
50. G. C. Bignan, K. Battista, P. J. Connolly, M. J. Orsini, J. C. Liu, S. A. Middleton, A. B. Reitz, Bioorg. Med. Chem. Lett., 2005, 15, 5022
51. C. V. Galliford, K. A. Scheidt, Angew. Chem., Int. Ed., 2007, 46, 8748
52. S. Kotha, A. C. Deb, K. Lahiri, E. Manivannan, Synthesis, 2009, 165
53. A. B. Dounay, L. E. Overman, Chem. Rev., 2003, 103, 2945
54. C. V. Galliford, K. A. Scheidt, Angew. Chem., Int. Ed., 2007, 46, 8748
55. G. S. Singh, M. Dhooghe, N. De Kimpe, Chem. Rev., 2007, 107, 2080
56. F. Zhou, Y.-L. Liu, J. Zhou, Adv. Synth. Catal., 2010, 352, 1381
57. K. Shen, X. Liu, L. Lin, X.-M. Feng, Chem. Sci., 2012, 3, 327
58. J. E. M. N. Klein, R. J. K. Taylor, Eur. J. Org. Chem., 2011, 6821
59. G. S. Singh, Z. Y. Desta, Chem. Rev., 2012, 112, 6104
60. N. R. Ball-Jones, J. J. Badillo, A. K. Franz, Org. Biomol. Chem., 2012, 10, 5165
61. H.-B. Yang, M. Shi, Org. Biomol. Chem., 2012, 10, 8236
62. Z. Lian, M. Shi, Org. Biomol. Chem., 2012, 10, 8048
63. Z. Lian, M. Shi, Eur. J. Org. Chem., 2012, 581
64. Z. Lian, M. Shi, Tetrahedron, 2012, 68, 2401
65. H.-B. Yang, X.-Y. Guan, Y. Wei, M. Shi, Eur. J. Org. Chem., 2012, 2792
66. D. Du, Y. Jiang, Q. Xu, M. Shi, Adv. Synth. Catal., 2013, 355, 2249
67. Q. Wang, Z. Lian, Q. Xu, M. Shi, Adv. Synth. Catal., 2013, 355, 3344
68. L.-Y. Mei, Y. Wei, Q. Xu, M. Shi, Organometallics, 2012, 31, 7591
69. X.-N. Zhang, G.-Q. Chen, X. Dong, Y. Wei, M. Shi, Adv. Synth. Catal., 2013, 355, 3351
70. F.-L. Hu, Y. Wei, M. Shi, Adv. Synth. Catal., 2014, 356, 736
71. Y.-L. Yang, C.-K. Pei, M. Shi, Org. Biomol. Chem., 2011, 9, 3349
72. R. Zhou, C. Wang, H. Song, Z. He, Org. Lett., 2010, 12, 976