Organocatalytic diastereo- and enantioselective 1,3-dipolar cycloaddition of azlactones and methyleneindolinones

Angewandte Chemie - International Edition

Volumn 52, Issue 33, 2013, Pages 8633-8637

  Sun, Wangsheng ^a   Zhu, Gongming ^a   Wu, Chongyang ^a   Li, Guofeng ^a   Hong, Liang ^a   Wang, Rui ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

1,3 dipolar cycloaddition; asymmetric synthesis; azlactones; methyleneindolinones; organocatalysis

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; ASYMMETRIC SYNTHESIS; AZLACTONES; METHYLENEINDOLINONES; ORGANOCATALYSIS;

ENANTIOSELECTIVITY; REACTION KINETICS;

CYCLOADDITION;

HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; LACTONE; SPIRO COMPOUND;

1,3-DIPOLAR CYCLOADDITION; ARTICLE; ASYMMETRIC SYNTHESIS; AZLACTONES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; CYCLOADDITION; METHYLENEINDOLINONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOCATALYSIS; STEREOISOMERISM;

1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC SYNTHESIS; AZLACTONES; METHYLENEINDOLINONES; ORGANOCATALYSIS;

AZA COMPOUNDS; CATALYSIS; CYCLIZATION; CYCLOADDITION REACTION; INDOLES; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84882411324     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201302831     Document Type: Article

References (81)

1. J. Plöchl, Ber. Dtsch. Chem. Ges. 1883, 16, 2815
2. E. Erlenmeyer, Ber. Dtsch. Chem. Ges. 1900, 33, 2036; for reviews, see
3. J. S. Fisk, R. A. Mosey, J. J. Tepe, Chem. Soc. Rev. 2007, 36, 1432
4. N. M. Hewlett, C. D. Hupp, J. J. Tepe, Synthesis 2009, 2825
5. R. A. Mosey, J. S. Fisk, J. J. Tepe, Tetrahedron: Asymmetry 2008, 19, 2755
6. A.-N. R. Alba, R. Rios, Chem. Asian J. 2011, 6, 720.
7. J. C. Ruble, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 11532
8. S. A. Shaw, P. Aleman, E. Vedejs, J. Am. Chem. Soc. 2003, 125, 13368
9. S. A. Shaw, P. Aleman, J. Christy, J. W. Kampf, P. Va, E. Vedejs, J. Am. Chem. Soc. 2006, 128, 925
10. C. Joannesse, C. P. Johnston, C. Concellón, C. Simal, D. Philp, A. D. Smith, Angew. Chem. 2009, 121, 9076
11. Angew. Chem. Int. Ed. 2009, 48, 8914
12. C. Kanta De, N. Mittal, D. Seidel, J. Am. Chem. Soc. 2011, 133, 16802
13. B. M. Trost, C. Jäkel, B. Plietker, J. Am. Chem. Soc. 2003, 125, 4438
14. B. M. Trost, X. Ariza, J. Am. Chem. Soc. 1999, 121, 10727
15. B. M. Trost, C. B. Lee, J. Am. Chem. Soc. 1998, 120, 6818
16. B. M. Trost, K. Dogra, J. Am. Chem. Soc. 2002, 124, 7256
17. D. Uraguchi, Y. Asai, T. Ooi, Angew. Chem. 2009, 121, 747
18. Angew. Chem. Int. Ed. 2009, 48, 733
19. M. Weber, S. Jautze, W. Frey, R. Peters, Chem. Eur. J. 2012, 18, 14792.
20. D. Uraguchi, Y. Ueki, T. Ooi, J. Am. Chem. Soc. 2008, 130, 14088
21. D. Uraguchi, K. Koshimoto, T. Ooi, Chem. Commun. 2010, 46, 300
22. X. Liu, L. Deng, X. Jiang, W. Yan, C. Liu, R. Wang, Org. Lett. 2010, 12, 876
23. X. Liu, L. Deng, H. Song, H. Jia, R. Wang, Org. Lett. 2011, 13, 1494
24. S.-H. Shi, F.-P. Huang, P. Zhu, Z.-W. Dong, X.-P. Hui, Org. Lett. 2012, 14, 2010
25. W.-Q. Zhang, L.-F. Cheng, J. Yu, L.-Z. Gong, Angew. Chem. 2012, 124, 4161
26. Angew. Chem. Int. Ed. 2012, 51, 4085; for aldol-type reactions, see
27. M. Terada, H. Tanaka, K. Sorimachi, J. Am. Chem. Soc. 2009, 131, 3430
28. T. Misaki, G. Takimoto, T. Sugimura, J. Am. Chem. Soc. 2010, 132, 6286.
29. S. Cabrera, E. Reyes, J. Alemán, A. Milelli, S. Kobbelgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2008, 130, 12031
30. J. Alemán, A. Milelli, S. Cabrera, E. Reyes, K. A. Jørgensen, Chem. Eur. J. 2008, 14, 10958
31. H. Jiang, M. W. Paixão, D. Monge, K. A. Jørgensen, J. Am. Chem. Soc. 2010, 132, 2775
32. D. Uraguchi, Y. Ueki, T. Ooi, Science 2009, 326, 120
33. A.-N. R. Alba, G. Valero, T. Calbet, M. Font-Bardía, A. Moyano, R. Rios, Chem. Eur. J. 2010, 16, 9884
34. A.-N. R. Alba, X. Companyó, G. Valero, A. Moyano, R. Rios, Chem. Eur. J. 2010, 16, 5354
35. D. Uraguchi, Y. Ueki, A. Sugiyama, T. Ooi, Chem. Sci. 2013, 4, 1308.
36. S. Dong, X. Liu, X. Chen, F. Mei, Y. Zhang, B. Gao, L. Lin, X. Feng, J. Am. Chem. Soc. 2010, 132, 10650
37. S. Dong, X. Liu, Y. Zhang, L. Lin, X. Feng, Org. Lett. 2011, 13, 5060
38. J. Jiang, J. Qing, L.-Z. Gong, Chem. Eur. J. 2009, 15, 7031
39. M. Terada, H. Nii, Chem. Eur. J. 2011, 17, 1760
40. Y. Ying, Z. Chai, H.-F. Wang, P. Li, C.-W. Zheng, G. Zhao, Y.-P. Cai, Tetrahedron 2011, 67, 3337
41. X. Jiang, H. Zhu, X. Shi, Y. Zhong, Y. Li, R. Wang, Adv. Synth. Catal. 2013, 355, 308.
42. V. Sharma, J. J. Tepe, Org. Lett. 2005, 7, 5091
43. R. S. Z. Saleem, J. J. Tepe, J. Org. Chem. 2010, 75, 4330
44. S. Peddibhotla, J. J. Tepe, Synthesis 2003, 1433
45. S. Peddibhotla, J. J. Tepe, J. Am. Chem. Soc. 2004, 126, 12776.
46. 1,3-Dipolar Cycloaddition Chemistry (Ed.:, A. Padwa,), Wiley, New York, 1984
47. A. Padwa, W. Pearson, Synthetic Applications of Dipolar Cycloaddition Chemistry towards Heterocyclic and Natural Products, Wiley-VCH, Weinheim, 2002
48. L. M. Stanley, M. P. Sibi, Chem. Rev. 2008, 108, 2887
49. K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863
50. G. Pandey, P. Banerjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484.
51. A. D. Melhado, M. Luparia, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 12638
52. A. D. Melhado, G. W. Amarante, Z. J. Wang, M. Luparia, F. D. Toste, J. Am. Chem. Soc. 2011, 133, 3517
53. M. Martín-Rodríguez, C. Nájera, J. M. Sansano, Synlett 2012, 62.
54. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902
55. Angew. Chem. Int. Ed. 2007, 46, 8748
56. C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209
57. H. Lin, S. J. Danishefsky, Angew. Chem. 2003, 115, 38
58. Angew. Chem. Int. Ed. 2003, 42, 36
59. K. Ding, Y. Lu, Z. Nikolovska-Coleska, S. Qiu, Y. Ding, W. Gao, J. Stuckey, K. Krajewski, P. P. Roller, Y. Tomita, D. A. Parrish, J. R. Deschamps, S. Wang, J. Am. Chem. Soc. 2005, 127, 10130
60. S. Shangary, D. Qin, D. McEachern, M. Liu, R. S. Miller, S. Qiu, Z. Nikolovska-Coleska, K. Ding, G. Wang, J. Chen, D. Bernard, J. Zhang, Y. Lu, Q. Gu, R. B. Shah, K. J. Pienta, X. Ling, S. Kang, M. Guo, Y. Sun, D. Yang, S. Wang, Proc. Natl. Acad. Sci. USA 2008, 105, 3933.
61. B. M. Trost, M. K. Brennan, Synthesis 2009, 3003
62. G. S. Singh, Z. Y. Desta, Chem. Rev. 2012, 112, 6104
63. R. Dalpozzo, G. Bartoli, G. Bencivenni, Chem. Soc. Rev. 2012, 41, 7247
64. N. R. Ball-Jones, J. J. Badillo, A. K. Franz, Org. Biomol. Chem. 2012, 10, 5165
65. F. Zhou, Y.-L. Liu, J. Zhou, Adv. Synth. Catal. 2010, 352, 1381
66. L. Hong, R. Wang, Adv. Synth. Catal. 2013, 355, 1023.
67. A. P. Antonchick, C. Gerding-Reimers, M. Catarinella, M. Schürmann, H. Preut, S. Ziegler, D. Rauh, H. Waldmann, Nat. Chem. 2010, 2, 735
68. X.-H. Chen, Q. Wei, S.-W. Luo, H. Xiao, L.-Z. Gong, J. Am. Chem. Soc. 2009, 131, 13819
69. F. Shi, Z.-L. Tao, S.-W. Luo, S.-J. Tu, L.-Z. Gong, Chem. Eur. J. 2012, 18, 6885
70. L.-L. Wang, J.-F. Bai, L. Peng, L.-W. Qi, L.-N. Jia, Y.-L. Guo, X.-Y. Luo, X.-Y. Xu, L.-X. Wang, Chem. Commun. 2012, 48, 5175
71. B. Tan, X. Zeng, W. W. Y. Leong, Z. Shi, C. F. Barbas III, G. Zhong, Chem. Eur. J. 2012, 18, 63.
72. X. Jiang, Y. Cao, Y. Wang, L. Liu, F. Shen, R. Wang, J. Am. Chem. Soc. 2010, 132, 15328
73. Y. Cao, X. Jiang, L. Liu, F. Shen, F. Zhang, R. Wang, Angew. Chem. 2011, 123, 9290
74. Angew. Chem. Int. Ed. 2011, 50, 9124
75. W. Sun, G. Zhu, C. Wu, L. Hong, R. Wang, Chem. Eur. J. 2012, 18, 6737
76. X. Jiang, Y. Sun, J. Yao, Y. Cao, M. Kai, N. He, X. Zhang, Y. Wang, R. Wang, Adv. Synth. Catal. 2012, 354, 917
77. W. Sun, G. Zhu, C. Wu, L. Hong, R. Wang, Chem. Eur. J. 2012, 18, 13959
78. Y.-M. Cao, F.-F. Shen, F.-T. Zhang, R. Wang, Chem. Eur. J. 2013, 19, 1184
79. Q. Chen, J. Liang, S. Wang, D. Wang, R. Wang, Chem. Commun. 2013, 49, 1657
80. L. Hong, M. Kai, C. Wu, W. Sun, G. Zhu, G. Li, X. Yao, R. Wang, Chem. Commun. 2013, DOI:.
81. CCDC 932360 (5 b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.