Diastereoconvergent synthesis of trans -5-hydroxy-6-substituted-2- piperidinones by addition-cyclization-deprotection process

Organic Letters

Volumn 16, Issue 16, 2014, Pages 4328-4331

  Si, Chang Mei ^a,b   Huang, Wei ^a   Du, Zhen Ting ^b   Wei, Bang Guo ^a   Lin, Guo Qiang ^a  

^a FUDAN UNIVERSITY   (China)

^b NORTHWEST A F UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2-PIPERIDONE; 3-(2-METHOXYBENZYLAMINO)-2-PHENYLPIPERIDINE; PIPERIDINE DERIVATIVE; PIPERIDONE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; MOLECULAR STRUCTURE; PIPERIDINES; PIPERIDONES; STEREOISOMERISM;

EID: 84906242079     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5020812     Document Type: Article

References (62)

1. Ojima, I. Catalytic Asymmetric Synthesis; Wiley-VCH: Weinheim, 2000.
2. Tsuji, J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 2000.
3. Liu, L.-X.; Ruan, Y.-P.; Guo, Z.-Q.; Huang, P.-Q. J. Org. Chem. 2004, 69, 6001
4. Andrés, J. M.; Pedrosa, R.; Pérez-Encabo, A. Tetrahedron Lett. 2006, 47, 5317
5. González, A. S.; Arrayás, R. G.; Rivero, M. R.; Carretero, J. C. Org. Lett. 2008, 10, 4335
6. Garrido, M.; García, M.; Sánchez, M. R.; Díez, D.; Urones, J. G. SYNLETT 2010, 387
7. Prévost, S.; Phansavath, P.; Haddad, M. Tetrahedron: Asymmetry 2010, 21, 16
8. Ruan, S.-T.; Luo, J.-M.; Du, Y.; Huang, P.-Q. Org. Lett. 2011, 13, 4938
9. Tan, C. K.; Le, C.; Yeung, Y.-Y. Chem. Commun. 2012, 48, 5793
10. Pansare, S. V.; Paul, E. K. Org. Biomol. Chem. 2012, 10, 2119
11. Archibald, G.; Lin, C.-P.; Boyd, P.; Barker, D.; Caprio, V. J. Org. Chem. 2012, 77, 7968
12. Huy, P. H.; Koskinen, A. M. P. Org. Lett. 2013, 15, 5178
13. Huy, P. H.; Westphal, J. C.; Koskinen, A. M. P. Beilstein J. Org. Chem. 2014, 10, 369
14. Koepfli, J. B.; Mead, J. F.; Brockman, J. A., Jr. J. Am. Chem. Soc. 1947, 69, 1837
15. Ratle, G.; Monseur, X.; Das, B. C.; Yassi, J.; Khuong-Huu, Q.; Goutarel, R. Bull. Soc. Chim. Fr. 1966, 9, 2945
16. Desai, M. C.; Lefkowitz, S. L.; Thadeio, P. F.; Longo, K. P.; Snider, R. M. J. Med. Chem. 1992, 35, 4911
17. Guengerich, F. P.; DiMari, S. J.; Broquist, H. P. J. Am. Chem. Soc. 1973, 95, 2055
18. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435
19. Reynolds, T. Phytochemistry 2005, 66, 1399
20. Remuson, R.; Gelas-Mialhe, Y. Mini-Rev. Org. Chem. 2008, 5, 193
21. Buffat, M. G. P. Tetrahedron 2004, 60, 1701
22. Escolano, C.; Amat, M.; Bosch, J. Chem. - Eur. J. 2006, 12, 8199
23. Kallstrom, S.; Leino, R. Bioorg. Med. Chem. 2008, 16, 601
24. Zhou, P.; Chen, B. C.; Davis, F. A. Tetrahedron 2004, 60, 8003
25. Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869
26. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984
27. Lin, G. Q.; Xu, M. H.; Zhong, Y. W.; Sun, X. W. Acc. Chem. Res. 2008, 41, 831
28. Ferreira, F.; Botuha, C.; Chemla, F.; Perez-Luna, A. Chem. Soc. Rev. 2009, 38, 1162
29. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600
30. Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396
31. Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772
32. Staas, D. D.; Savage, K. L.; Homnick, C. F.; Tsou, N. N.; Ball, R. G. J. Org. Chem. 2002, 67, 8276
33. Zhong, Y. W.; Dong, Y. Z.; Fang, K.; Izumi, K.; Xu, M. H.; Lin, G. Q. J. Am. Chem. Soc. 2005, 127, 11956
34. Barrett, G. C. Chemistry and Biochemistry of the Amino Acids; Chapman & Hall: London, 1985.
35. Jones, J. Amino Acid and Peptide Synthesis; Oxford University Press: London, 1992.
36. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995.
37. Blaser, H. U. Chem. Rev. 1992, 92, 935
38. Xarnod, C.; Huang, W.; Ren, R. G.; Liu, R. C.; Wei, B. G. Tetrahedron 2012, 68, 6688
39. Huang, W.; Ye, J. L.; Zheng, W.; Dong, H. Q.; Wei, B. G. J. Org. Chem. 2013, 78, 11229
40. Evans, J. W.; Ellman, J. A. J. Org. Chem. 2003, 68, 9948
41. Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1780
42. Winkler, J. W.; Uddin, J.; Serhan, C. N.; Petasis, N. A. Org. Lett. 2013, 15, 1424
43. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155
44. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277
45. Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537
46. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268
47. Liu, G. C.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278
48. Chandrasekhar, S.; Mohanty, P. K. Tetrahedron Lett. 1999, 40, 5071
49. Yamazaki, N.; Atobe, M.; Kibayashi, C. Tetrahedron Lett. 2002, 43, 7979
50. Tsuritani, N.; Yamada, K.; Yoshikawa, N.; Shibasaki, M. Chem. Lett. 2002, 276
51. Huang, P. Q.; Liu, L. X.; Wei, B. G.; Ruan, Y. P. Org. Lett. 2003, 5, 1927
52. Atobe, M.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 2004, 69, 5595
53. Oshitari, T.; Mandai, T. Synlett 2006, 3395
54. Davis, F. A.; Zhang, Y. F.; Li, D. Y. Tetrahedron Lett. 2007, 48, 7838
55. Liu, R. H.; Fang, K.; Wang, B.; Xu, M. H.; Lin, G. Q. J. Org. Chem. 2008, 73, 3307
56. Fu, R. Z.; Zhao, B. G.; Shi, Y. J. Org. Chem. 2009, 74, 7577
57. Garrido, N. M.; Garcia, M.; Sanchez, M. R.; Diez, D.; Urones, J. G. Synlett 2010, 387
58. Pansare, S. V.; Paul, E. K. Org. Biomol Chem. 2012, 10, 2119
59. Sultane, P. R.; Bhat, R. G. J. Org. Chem. 2012, 77, 11349
60. Lemire, A.; Grenon, M.; Pourashraf, M.; Charette, A. B. Org. Lett. 2004, 6, 3517
61. Takahashi, K.; Nakano, H.; Fujita, R. Tetrahedron Lett. 2005, 46, 8927
62. Xu, X. N.; Furukawa, T.; Okino, T.; Miyabe, H.; Takemoto, Y. Chem. - Eur. J. 2006, 12, 466