An efficient synthesis of 2- and 2,6-substituted piperidines using Pd II-catalyzed 1,3-chirality transfer reaction

Journal of Organic Chemistry

Volumn 74, Issue 1, 2009, Pages 244-253

  Hande, Sudhir M ^a   Kawai, Nobuyuki ^a   Uenishi, Jun'ichi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOLS; CHEMICAL EQUATIONS; CHIRALITY TRANSFERS; EFFICIENT SYNTHESES; GENERAL METHODS; REACTION PATHWAYS;

AMINES; CHEMICAL REACTIONS; CHIRALITY; ENANTIOMERS; ORGANIC POLYMERS; PALLADIUM; PALLADIUM COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PIPERIDINES; STEREOISOMERISM;

EID: 58149293589     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801926g     Document Type: Article

References (68)

1. Recent reviews: (a) Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953-2989.
2. (b) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892.
3. (c) Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 633-640.
4. (d) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8.
5. (e) Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383-394.
6. (f) Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781-1813.
7. (g) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
8. (h) Buffat, M. G. P. Tetrahedron 2004, 60, 1701-1729.
9. (i) Escolano, C.; Amat, M.; Bosch, J. Chem. - Eur. J. 2006, 12, 8198-8202.
10. (a) Wolffenstein, R. Ber. 1894, 27, 2611-2615.
11. (b) Ahrens, F. B. Ber. 1902, 35, 1330-1334.
12. (c) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P J. Am. Chem. Soc. 1983, 105, 7754-7755.
13. (d) Sanchez-Sancho, F.; Herradon, B. Tetrahedron: Asymmetry 1998, 9, 1951-1956.
14. (a) Krochmal, A. Lloydia 1972, 35, 303-304.
15. (b) Flammia, D.; Dukat, M.; Damaj, M. I.; Martin, B.; Glennon, R. A. J. Med. Chem. 1999, 42, 3726-3731.
16. (c) Felpin, F.-X.; Lebreton, J. Tetrahedron 2004, 60, 10127-10153.
17. (a) Edwards, M. W.; Daly, J. W. J. Nat. Prod. 1988, 51, 1188-1197.
18. (b) Edwards, M. W.; Garraffo, H. M.; Daly, J. W. Synthesis 1994, 1167-1170.
19. (c) Girard, N.; Hurvois, J.-P. Tetrahedron Lett. 2007, 48, 4097-4099, and references therein.
20. (a) Highet, R. J. J. Org. Chem. 1964, 29, 471-474.
21. (b) Rice, W. Y., Jr.; Coke, J. L. J. Org. Chem. 1966, 31, 1010-1012.
22. (a) Rougnon-Glasson, S.; Tratrat, C.; Canet, J.-L.; Chalard, P.; Train, Y. Tetrahedron: Asymmetry 2004, 15, 1561-1567.
23. (b) Bariau, A.; Jatoi; W, B.; Calinaud, P.; Train, Y.; Canet, J.-L. Eur. J. Org. Chem. 2006, 3421-3433.
24. (c) Carbonnel, S.; Fayet, C.; Gelas, J.; Train, Y. Tetrahedron Lett. 2000, 41, 8293-8296.
25. (d) Rougnon-Glasson, S.; Canet, J.-L.; Train, Y. Tetrahedron Lett. 2000, 41, 9797-9802.
26. (a) Stockman, R. A. Tetrahedron Lett. 2000, 41, 9163-9165.
27. (b) McAlpine, I. J.; Armstrong, R. W. Tetrahedron Lett. 2000, 41, 1849-1853.
28. (a) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693-3612.
29. (b) Dolman, S. J.; Sattely, E. S.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 2002, 124, 6991-6994.
30. (c) Wallace, D. J.; Goodman, J. M.; Kennedy, D. J.; Davies, A. J.; Cowden, C. J.; Ashwood, M. S.; Cottrell, I. F.; Dolling, U.; Reider, P. J. Org. Lett. 2001, 5, 671-674.
31. (a) Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2000, 65, 4435-4439.
32. (b) Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 2424-2428.
33. Recent reviews: (a) Buonora, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099-6138.
34. (b) Jorgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558-3588.
35. (c) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 17, 2913-2916.
36. (a) Hosokawa, T. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley and Sons: New York, 2002; Vol. 2., pp 2211-2225.
37. (b) Cacchi, S.; Marinelli, F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley and Sons: New York, 2002; Vol. 2., pp 2227-2243.
38. For example (a) Overmann, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2001, 124, 12-13.
39. (b) Makabe, H.; Kong, L. K.; Hirota, M. Org. Lett. 2003, 5, 27-29.
40. (c) Minatti, A.; Muniz, K. Chem. Soc. Rev. 2007, 36, 1142-1152.
41. (a) Muniz, K. J. Am. Chem. Soc. 2007, 129, 14542-14543.
42. (b) Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690-7691.
43. (a) Muniz, K.; Hövelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763-773.
44. (b) Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179-7181.
45. (c) Brice, J. B.; Harang, J. E.; Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 2868-2869.
46. (d) Ney, J. E.; Wolfe, J. P. Angew. Chem., Int. Ed. 2004, 43, 3605-3608.
47. Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2007, 129, 6328-6335.
48. (a) Uenishi, J.; Ohmi, M.; Ueda, A. Tetrahedron: Asymmetry 2005, 16, 1299-1303.
49. (b) Kawai, N.; Lagrange, J. M.; Ohmi, M.; Uenishi, J. J. Org. Chem. 2006, 71, 4530-4537.
50. (c) Uenishi, J.; Vikhe, Y. S.; Kawai, N. Chem. Asian. J. 2008, 3, 473-484.
51. (a) Hayashi, T.; Yamasaki, K.; Mimura, M.; Uozumi, Y. J. Am. Chem. Soc. 2004, 126, 3036-3037.
52. (b) Zhang, Z.; Pan, C.; Wang, Z. Chem. Commun. 2007, 4686-4688.
53. (c) Trend, R. M.; Ramtohul, Y. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 17778-17788.
54. (d) Sharma, G V. M.; Chander, A. S.; Krishnudu, K.; Krishna, P. R. Tetrahedron Lett. 1998, 39, 6957-6960.
55. (e) Benthem, R. A. T. M.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1992, 57, 6083-6085.
56. (a) Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777.
57. (b) Yokoyama, H.; Otaya, K.; Kobayashi, H.; Miyazawa, M.; Yamaguchi, S.; Hirai, Y. Org. Lett. 2000, 2, 2427-2429.
58. (c) Yokoyama, H.; Ejiri, H.; Miyazawa, M.; Yamaguchi, S.; Hirai, Y. Tetrahedron: Asymmetry 2007, 18, 852-856.
59. Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700-709.
60. Rix, D.; Caijo, F.; Laurent, I.; Boeda, F.; Clavier, H.; Nolan, P. N.; Mauduit, M. J. Org. Chem. 2008, 73, 4225-4228.
61. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, Third ed.; John Wiley and Sons: New York, 1999.
62. Wilson, S. R.; Augelli-Szafran, C. E. Tetrahedron 1988, 44, 3983-3995.
63. Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056-9062.
64. Hirai, Y.; Nagatsu, M. Chem. Lett. 1994, 23, 21-22.
65. Hong, S.; Kawaoka, A. M.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 15878-15892.
66. Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807.
67. Drian, C. L.; Greene, A. E. J. Am. Chem. Soc. 1982, 104, 5473-5483.
68. The possibility of anti-coordination of Pd with respect to the chiral hydroxy group is not considered here. The argument of this possibility was discussed well in the case of oxy-palladation reaction in the previous article. See ref 16c.