Chiral phosphoric acid-catalyzed enantioselective three- component aza-diels-alder reactions of aminopyrroles and aminopyrazoles

Advanced Synthesis and Catalysis

Volumn 356, Issue 8, 2014, Pages 1719-1724

  Brioche, Julien ^a   Courant, Thibaut ^a   Alcaraz, Lilian ^b   Stocks, Michael ^b   Furber, Mark ^b   Zhu, Jieping ^c   Masson, Géraldine ^a  

^a CNRS   (France)

^b ASTRAZENECA R AND D   (Sweden)

^c EPFL   (Switzerland)

Author keywords

asymmetric synthesis; aza Diels Alder reaction; chiral phosphoric acid; organocatalysis; Povarov reaction

Indexed keywords

EID: 84901285780     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400093     Document Type: Article

References (74)

1. For reviews, see:, M. Rubiralta, E. Giralt, A. Diez, Piperidine: Structure, Preparation and Synthetic Applications of Piperidine and its Derivatives, Elsevier, Amsterdam, 1991
2. Modern Alkaloids: Structure, Isolation, Synthesis and Biology, (Eds.:, E. Fattorusso, O. Taglialatela-Scafati,), Wiley-VCH, Weinheim, Germany, 2008
3. M. G. P. Buffat, Tetrahedron 2004, 60, 1701
4. V. Farina, J. T. Reeves, C. H. Senanayake, J. J. Song, Chem. Rev. 2006, 106, 2734.
5. Asymmetric Synthesis of Nitrogen Heterocycles, (Ed.:, J. Royer,), Wiley-VCH, Weinheim, Germany, 2009; for recent examples, see
6. M. Yamashita, K.-i. Yamada, K. Tomioka, J. Am. Chem. Soc. 2004, 126, 1954
7. J. Franzén, A. Fisher, Angew. Chem. 2009, 121, 801
8. Angew. Chem. Int. Ed. 2009, 48, 787
9. W. Zhang, J. Franzén, Adv. Synth. Catal. 2010, 352, 499
10. S.-L. Zhou, J.-L. Li, L. Dong, Y.-C. Chen, Org. Lett. 2011, 13, 5874
11. C. Ma, J. Gu, B. Teng, Q.-Q. Zhou, R. Li, Y.-C. Chen, Org. Lett. 2013, 15, 6206.
12. V. A. Glushkov, A. G. Tolstikov, Russ. Chem. Rev. 2008, 77, 137
13. V. V. Kouznetsov, Tetrahedron 2009, 65, 2721
14. D. Bello, R. Ramõn, R. Lavilla, Curr. Org. Chem. 2010, 14, 332
15. V. Sridharan, P. A. Suryavanshi, J. C. Menendez, Chem. Rev. 2011, 111, 7157
16. X. X. Jiang, R. Wang, Chem. Rev. 2013, 113, 5515
17. G. Masson, C. Lalli, M. Benohoud, G. Dagousset, Chem. Soc. Rev. 2013, 42, 902
18. M. Fochi, L. Caruana, L. Bernardi, Synthesis 2014, 46, 135.
19. H. Ishitani, S. Kobayashi, Tetrahedron Lett. 1996, 37, 7357
20. G. Sundararajan, N. Prabagaran, B. Varghese, Org. Lett. 2001, 3, 1973
21. T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070.
22. M. S. Xie, X. H. Chen, Y. Zhu, B. Gao, L. L. Lin, X. H. Liu, X. M. Feng, Angew. Chem. 2010, 122, 3887
23. Angew. Chem. Int. Ed. 2010, 49, 3799
24. M. S. Xie, X. H. Liu, Y. Zhu, X. H. Zhao, Y. Xia, L. L. Lin, X. M. Feng, Chem. Eur. J. 2011, 17, 13800.
25. H. Liu, G. Dagousset, G. Masson, P. Retailleau, J. P. Zhu, J. Am. Chem. Soc. 2009, 131, 4598
26. C. Wang, Z. Y. Han, H. W. Luo, L. Z. Gong, Org. Lett. 2010, 12, 2266
27. A. H. Xu, S. J. Zuend, M. G. Woll, Y. Tao, E. N. Jacobsen, Science 2010, 327, 986
28. G. Dagousset, J. P. Zhu, G. Masson, J. Am. Chem. Soc. 2011, 133, 14804
29. J. H. Lin, G. Q. Zong, R. B. Du, J. C. Xiao, S. B. Liu, Chem. Commun. 2012, 48, 7738
30. G. Dagousset, P. Retailleau, G. Masson, J. P. Zhu, Chem. Eur. J. 2012, 18, 5869
31. C. Min, N. Mittal, D. X. Sun, D. Seidel, Angew. Chem. 2013, 125, 14334
32. Angew. Chem. Int. Ed. 2013, 52, 14084
33. L. Caruana, M. Fochi, S. Ranieri, A. Mazzanti, L. Bernardi, Chem. Commun. 2013, 49, 880
34. D. Huang, F. Xu, T. Chen, Y. Wang, X. Lin, RSC Adv. 2013, 3, 573.
35. Z. L. Chen, B. L. Wang, Z. B. Wang, G. Y. Zhu, J. W. Sun, Angew. Chem. 2013, 125, 2081
36. Angew. Chem. Int. Ed. 2013, 52, 2027
37. C. S. Luo, Y. Huang, J. Am. Chem. Soc. 2013, 135, 8193.
38. G. Bergonzini, L. Gramigna, A. Mazzanti, M. Fochi, L. Bernardi, A. Ricci, Chem. Commun. 2010, 46, 327.
39. L. He, M. Bekkaye, P. Retailleau, G. Masson, Org. Lett. 2012, 14, 3158
40. F. Shi, G.-J. Xing, Z.-L. Tao, S.-W. Luo, S.-J. Tu, L.-Z. Gong, J. Org. Chem. 2012, 77, 6970
41. F. Shi, G. J. Xing, R. Y. Zhu, W. Tan, S. J. Tu, Org. Lett. 2013, 15, 128.
42. M. De Rosa, R. P. Issac, G. Houghton, Tetrahedron Lett. 1995, 36, 9261
43. G. Cirrincione, A. M. Almerico, P. Diana, P. Barraja, F. Mingoia, S. Grimaudo, G. Dattolo, E. Aiello, J. Heterocycl. Chem. 1996, 33, 131
44. M. De Rosa, R. P. Issac, M. Marquez, M. Orozco, F. J. Luque, M. D. Timken, J. Chem. Soc. Perkin Trans. 2 1999, 1433.
45. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999
46. T. Akiyama, Chem. Rev. 2007, 107, 5744
47. M. Terada, Chem. Commun. 2008, 4097
48. M. Terada, Synthesis 2010, 1929
49. M. Terada, Bull. Chem. Soc. Jpn. 2010, 83, 101
50. D. Kampen, C. M. Reisinger, B. List, Top. Curr. Chem. 2010, 291, 395
51. M. Terada, Curr. Org. Chem. 2011, 15, 2227
52. M. Rueping, A. Kuenkel, I. Atodiresei, Chem. Soc. Rev. 2011, 40, 4539.
53. H. J. Andersan, Can. J. Chem. 1959, 37, 2053
54. A. R. Cooksey, K. J. Morgan, D. P. Morrey, Tetrahedron 1970, 26, 5101.
55. S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336
56. Z. Chai, T. J. Rainey, J. Am. Chem. Soc. 2012, 134, 3615.
57. The cis-stereochemistry was confirmed by NOESY of 9a (see the Supporting Information).
58. The trans-stereochemistry was established based on the results of NOESY experiments of 9i, 9j and 9k (see the Supporting information).
59. The epimerization of 9d may occur via a sequence of elimination and readdition of the carbamate.
60. L. Simõn, J. M. Goodman, J. Org. Chem. 2011, 76, 1775.
61. S. Kobayashi, H. Ishitani, S. Nakagawa, Synthesis 1995, 1195
62. S. Hermitage, D. A. Jayb, A. Whiting, Tetrahedron Lett. 2002, 43, 9633
63. P. J. Stevenson, I. Graham, ARKIVOC 2003, 139
64. I. Carranco, J. L. Díaz, O. Jiménez, R. Lavilla, Tetrahedron Lett. 2003, 44, 8849
65. V. Sridharan, C. Avendaño, J. Carlos Menéndez, Synthesis 2008, 1039
66. M. J. Alves, N. G. Azoia, A. G. Fortes, Tetrahedron 2007, 63, 727
67. N. Shindoh, H. Tokuyama, Y. Takemoto, K. Takasu, J. Org. Chem. 2008, 73, 7451.
68. O. Jiménez, G. de La Rosa, R. Lavilla, Angew. Chem. 2005, 117, 6679
69. Angew. Chem. Int. Ed. 2005, 44, 6521
70. N. Isambert, M. Cruz, M. J. Arévalo, E. Gõmez, R. Lavilla, Org. Lett. 2007, 9, 4199
71. L. Bernardi, M. Comes-Franchini, M. Fochi, V. Leo, A. Mazzanti, A. Ricci, Adv. Synth. Catal. 2010, 352, 3399
72. G. Dagousset, F. Drouet, G. Masson, J. Zhu, Org. Lett. 2009, 11, 5546
73. S. Preciado, E. Vicente-García, S. Llabrés, F. J. Luque, R. Lavilla, Angew. Chem. 2012, 124, 6980
74. Angew. Chem. Int. Ed. 2012, 51, 6874.