Bifunctional organocatalytic strategy for inverse-electron-demand diels-alder reactions: Highly efficient in-situ substrate generation and activation to construct azaspirocyclic skeletons

Angewandte Chemie - International Edition

Volumn 51, Issue 9, 2012, Pages 2084-2087

  Jiang, Xianxing ^a   Shi, Xiaomei ^a   Wang, Shoulei ^a   Sun, Tao ^a   Cao, Yiming ^a   Wang, Rui ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

asymmetric synthesis; cycloadditions; heterocycles; organocatalysis; synthetic methods

Indexed keywords

ASYMMETRIC SYNTHESIS; CYCLOADDITIONS; HETEROCYCLES; ORGANOCATALYSIS; SYNTHETIC METHODS;

MUSCULOSKELETAL SYSTEM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY;

HETEROCYCLIC COMPOUND; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CYCLIZATION; SYNTHESIS;

AZA COMPOUNDS; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLIZATION; SPIRO COMPOUNDS;

EID: 84863116616     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107716     Document Type: Article

References (68)

1. For selected recent reviews, see
2. S. Reymond, J. Cossy, Chem. Rev. 2008, 108, 5359
3. K. Ishihara, M. Fushimi, M. Akakura, Acc. Chem. Res. 2007, 40, 1049
4. E. J. Corey, Angew. Chem. 2002, 114, 1724
5. Angew. Chem. Int. Ed. 2002, 41, 1650
6. Y. Hayashi, in Cycloaddition Reactions in Organic Synthesis (Eds.:, S. Kobayashi, K.-A. Jøgensen,), Wiley-VCH, Weinheim, 2001, p.- 5.
7. H. Ishitani, S. Kobayashi, Tetrahedron Lett. 1996, 37, 7357.
8. For selected examples, see
9. M. Xie, X. Chen, Y. Zhu, B. Gao, L. Lin, X. Liu, X. Feng, Angew. Chem. 2010, 122, 3887
10. Angew. Chem. Int. Ed. 2010, 49, 3799
11. P. Li, H. Yamamoto, J. Am. Chem. Soc. 2009, 131, 16628
12. J. Esquivias, R. G. Arrayas, J. C. Carretero, J. Am. Chem. Soc. 2007, 129, 1480
13. R. C. Clark, S. S. Pfeiffer, D. L. Boger, J. Am. Chem. Soc. 2006, 128, 2587.
14. M. He, J. R. Struble, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 8418
15. T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070.
16. D. A. Nicewicz, D. W. C. MacMillan, Science 2008, 322, 77
17. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243.
18. K. Juhl, K. A. Jøgensen, Angew. Chem. 2003, 115, 1536
19. Angew. Chem. Int. Ed. 2003, 42, 1498.
20. For examples of enamine activation for the IEDDAR, see
21. J. L. Li, T. R. Kang, S. L. Zhou, R. Li, L. Wu, Y. C. Chen, Angew. Chem. 2010, 122, 6562
22. Angew. Chem. Int. Ed. 2010, 49, 6418
23. B. Han, Z. Q. He, J. L. Li, R. Li, K. Jiang, T. Y. Liu, Y. C. Chen, Angew. Chem. 2009, 121, 5582
24. Angew. Chem. Int. Ed. 2009, 48, 5474
25. B. Han, J. L. Li, C. Ma, S. J. Zhang, Y. C. Chen, Angew. Chem. 2008, 120, 10119
26. Angew. Chem. Int. Ed. 2008, 47, 9971
27. H. Xie, L. Zu, H. R. Oueis, H. Li, J. Wang, W. Wang, Org. Lett. 2008, 10, 1923
28. S. Samanta, J. Krause, T. Mandal, C. G. Zhao, Org. Lett. 2007, 9, 2745.
29. For reviews, see
30. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713
31. S. J. Connon, Chem. Eur. J. 2006, 12, 5418
32. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550
33. Angew. Chem. Int. Ed. 2006, 45, 1520
34. Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299; For selected examples, see
35. K. L. Tan, E. N. Jacobsen, Angew. Chem. 2007, 119, 1337
36. Angew. Chem. Int. Ed. 2007, 46, 1315
37. S.-C. Pan, J. Zhou, B. List, Angew. Chem. 2007, 119, 618
38. Angew. Chem. Int. Ed. 2007, 46, 612
39. Y. Yamaoka, H. Miyabe, Y. Takemoto, J. Am. Chem. Soc. 2007, 129, 6686
40. L.-S. Zu, J. Wang, H. Li, H.-X. Xie, W. Jiang, W. Wang, J. Am. Chem. Soc. 2007, 129, 1036
41. S. Wei, D. A. Yalalov, S. B. Tsogoeva, S. Schmatz, Catal. Today 2007, 121, 151
42. S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451
43. D. A. Yalalov, S. B. Tsogoeva, S. Schmatz, Adv. Synth. Catal. 2006, 348, 826
44. R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. 2005, 117, 6734
45. Angew. Chem. Int. Ed. 2005, 44, 6576
46. S. H. McCooey, S. J. Connon, Angew. Chem. 2005, 117, 6525
47. Angew. Chem. Int. Ed. 2005, 44, 6367.
48. Z. Xu, L. Liu, K. Wheeler, H. Wang, Angew. Chem. 2011, 123, 3546
49. Angew. Chem. Int. Ed. 2011, 50, 3484.
50. For reviews on stereocontrolled synthesis of spirocycles, see
51. M. Sannigrahi, Tetrahedron 1999, 55, 9007
52. R. Pradhan, M. Patra, A. K. Behera, B. K. Mishra, R. K. Behera, Tetrahedron 2006, 62, 779
53. M. E. Sinibaldi, I. Canet, Eur. J. Org. Chem. 2008, 4391
54. S. Kotha, A. C. Deb, K. Lahiri, E. Manivannan, Synthesis 2009, 165.
55. For examples, see
56. K. A. Miller, S. Tsukamoto, R. M. Williams, Nat. Chem. 2009, 1, 63
57. X. Hong, S. France, J. M. MejÄa-Oneto, A. Padwa, Org. Lett. 2006, 8, 5141
58. D. G. Hilmey, L. A. Paquette, Org. Lett. 2005, 7, 2067
59. T. Fehr, J. Kallen, L. Oberer, J. J. Sanglier, W. Schilling, J. Antibiot. 1999, 52, 474.
60. For examples, see
61. J. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y. C. Chen, Y. Wu, J. Zhu, J. G. Deng, Angew. Chem. 2007, 119, 393
62. Angew. Chem. Int. Ed. 2007, 46, 389
63. N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368.
64. Y. M. Cao, X. X. Jiang, L. P. Liu, F. F. Shen, F. T. Zhang, R. Wang, Angew. Chem. 2011, 123, 9290
65. Angew. Chem. Int. Ed. 2011, 50, 9124
66. X. X. Jiang, Y. M. Cao, Y. Q. Wang, L. P. Liu, F. F. Shen, R. Wang, J. Am. Chem. Soc. 2010, 132, 15328.
67. S. J. Zuend, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 15872.
68. X. X. Jiang, Y. F. Zhang, A. S. C. Chan, R. Wang, Org. Lett. 2009, 11, 153.