NHC-catalysed diastereoselective synthesis of multifunctionalised piperidines via cascade reaction of enals with azalactones

Chemical Communications

Volumn 48, Issue 31, 2012, Pages 3766-3768

  Singh, Atul K ^a   Chawla, Ruchi ^a   Rai, Ankita ^a   Yadav, Lal Dhar S ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBENE; N HETEROCYCLIC CARBENE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ONE POT SYNTHESIS; RING OPENING; STEREOCHEMISTRY;

EID: 84860179135     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc00069e     Document Type: Article

References (62)

1. A. Berkessel and H. Gröger, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005
2. E. R. Jarvo, S. J. Miller, Tetrahedron, 2002, 58, 2481
3. P. I. Dalko, L. Moisan, Angew. Chem., Int. Ed., 2004, 43, 5138
4. B. List, J. Seayad, Org. Biomol. Chem., 2005, 3, 719
5. N. Marion, S. Díez-Gonzalez, S. P. Nolan, Angew. Chem., Int. Ed., 2007, 46, 2988
6. D. Enders, O. Niemeier, A. Henseler, Chem. Rev., 2007, 107, 5606
7. V. Nair, S. Vellalath, B. P. Babu, Chem. Soc. Rev., 2008, 37, 2691
8. E. M. Phillips, A. Chan, K. A. Scheidt, Aldrichimica Acta, 2009, 42, 55
9. J. L. Moore, T. Rovis, Top. Curr. Chem., 2010, 291, 77
10. T. Dreoge, F. Glorius, Nachr. Chem., 2010, 58, 112
11. T. Dreoge, F. Glorius, Angew. Chem., Int. Ed., 2010, 49, 6940
12. H. Stetter and H. Kuhlmann, Organic Reactions, ed. L. A. Paquette, Wiley, New York, 1991, p. 40
13. J. Read de Alaniz, T. Rovis, Synlett, 2009, 1189
14. S. S. Sohn, E. L. Rosen, J. W. Bode, J. Am. Chem. Soc., 2004, 126, 14370
15. C. Burstein, F. Glorius, Angew. Chem., Int. Ed., 2004, 43, 6205
16. A. Chan, K. A. Scheidt, Org. Lett., 2005, 7, 905
17. M. He, J. W. Bode, Org. Lett., 2005, 7, 3131
18. M. He, J. R. Struble, J. W. Bode, J. Am. Chem. Soc., 2006, 128, 8418
19. V. Nair, S. Vellalath, M. Poonoth, E. Suresh, J. Am. Chem. Soc., 2006, 128, 8736
20. P.-C. Chiang, J. Kaeobamrung, J. W. Bode, J. Am. Chem. Soc., 2007, 129, 3520
21. A. Chan, K. A. Scheidt, J. Am. Chem. Soc., 2008, 130, 2740
22. A.-N. R. Alba, R. Rios, Chem.–Asian J., 2011, 6, 720
23. R. A. Mosey, J. S. Fisk, J. J. Tepe, Tetrahedron: Asymmetry, 2008, 19, 2755
24. J. S. Fisk, R. A. Mosey, J. J. Tepe, Chem. Soc. Rev., 2007, 36, 1432
25. N. M. Hewlett, C. D. Hupp, J. J. Tepe, Synthesis, 2009, 2825
26. “Pharmaceutical Sales 2009”. Drug information online, Drugs.com. April 5, 2011: http://www.drugs.com/top200_units.html
27. P. D. Bailey, P. A. Millwood, P. D. Smith, Chem. Commun., 1998, 633
28. T. Komoto, K. Yano, J. Ono, J. Okawa and T. Nakajima, JP Patent, 61035788, 1986
29. Y. Takemoto, S. Ueda, J. Takeuchi, T. Nakmoto, C. Iwata, Tetrahedron Lett., 1994, 35, 8821
30. D. Lamarre, G. Croteau, L. Bourgon, D. Thibeault, E. Wardrop, C. Clouette, M. Vaillancourt, E. Cohen, C. Pargellis, C. Yoakim, P. Anderson, Antimicrob. Agents Chemother., 1997, 41, 965
31. V. Gorys, F. Soucy, C. Yoakim and P. L. Beaulieu, Eur. Patent, 560 269, 1993
32. P. C. Anderson, F. Soucy, C. Yoakim, P. Lavalle'e and P. L. Beaulieu, US Patent, 5 614 533, 1997
33. J. Jayabharathi, A. Manimekalai, T. Consalata Vani, M. Padmavathy, Eur. J. Med. Chem., 2007, 42, 593
34. P. S. Watson, B. Jiang, B. Scott, Org. Lett., 2000, 2, 3679
35. P. M. Weintraub, J. S. Sabol, J. M. Kane, D. R. Borcherding, Tetrahedron, 2003, 59, 2953
36. T. A. Johnson, M. D. Curtis, P. Break, J. Am. Chem. Soc., 2001, 123, 1004
37. S. Kallstrom, R. Leino, Bioorg. Med. Chem., 2008, 16, 601
38. T. Yamashita, K. Yasuda, H. Kizu, Y. Kameda, A. A. Watson, R. J. Nash, G. W. Fleet, N. Asano, J. Nat. Prod., 2002, 65, 1875
39. J. P. A. Harrity, O. Provoost, Org. Biomol. Chem., 2005, 3, 349
40. R. P. Hsung, A. V. Kurdyumov, N. Sydorenko, Eur. J. Org. Chem., 2005, 23
41. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem., Int. Ed., 2005, 44, 4212
42. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem., Int. Ed., 2005, 44, 794
43. M. Marigo, D. Fielenbach, A. Braunton, A. Kjasgaard, K. A. Jørgensen, Angew. Chem., Int. Ed., 2005, 44, 3703
44. C. Palomo, A. Mielgo, Angew. Chem., Int. Ed., 2006, 45, 7876
45. A. Mielgo, C. Palomo, Chem.–Asian J., 2008, 3, 922
46. Y. Hayashi, H. Gotoh, R. Masui, H. Shikawa, Angew. Chem., Int. Ed., 2008, 47, 4012
47. M. Amat, O. Lozano, C. Escolano, E. Molins, J. Bosch, J. Org. Chem., 2007, 72, 4431
48. M. Amat, N. Llor, J. Hidalgo, C. Escolano, J. Bosch, J. Org. Chem., 2003, 68, 1919
49. M. Amat, E. Brunaccini, B. A. Checa, M. Pérez, N. R. Llor, J. Bosch, Org. Lett., 2009, 11, 4370
50. Y. Nakamura, A. M. Burke, S. Kotani, J. W. Ziller, S. D. Rychnovsky, Org. Lett., 2009, 12, 72
51. D. Gnecco, A. M. Lumbreras, J. L. Teran, A. Galindo, J. R. Juarez, M. L. Orea, A. Castro, R. G. Enriquez, W. F. Reynolds, Heterocycles, 2009, 78, 2589
52. J. J. Verendel, T. G. Zhou, J. Q. Li, A. Paptchikhine, O. Lebedev, P. G. Andersson, J. Am. Chem. Soc., 2010, 132, 8880
53. S. B. D. Jarvis, A. B. Charette, Org. Lett., 2011, 13, 3830
54. T. Urushima, D. Sakamoto, H. Ishikawa, Y. Hayashi, Org. Lett., 2010, 12, 4588
55. L. D. S. Yadav, S. Singh, V. K. Rai, Synlett, 2010, 240-246
56. L. D. S. Yadav, V. K. Rai, S. Singh, P. Singh, Tetrahedron Lett., 2010, 51, 1657-1662
57. N. Rastogi, I. N. N. Namboothiri, M. Cojocaru, Tetrahedron Lett., 2004, 45, 4745
58. A. Rai, L. D. S. Yadav, Org. Biomol. Chem., 2011, 9, 8058
59. Y. Wang, D.-F. Yu, Y.-Z. Liu, H. Wei, Y.-C. Luo, D. J. Dixon, P.-F. Xu, Chem.–Eur. J., 2010, 16, 3922
60. T. Urushima, D. Sakamoto, H. Ishikawa, Y. Hayashi, Org. Lett., 2010, 12, 4588
61. Z.-Q. Liu, B.-K. Liu, Q. Wu, X.-F. Lin, Tetrahedron, 2011, 67, 9736
62. Y. Chen, C. Zhong, J. L. Peterson, N. G. Akhmedov, X. Shi, Org. Lett., 2009, 11, 2333