Catalytic asymmetric synthesis of piperidines from pyrrolidine: Concisesynthesis of L-733,060

Organic Letters

Volumn 11, Issue 9, 2009, Pages 1935-1938

  Bilke, Julia L ^a   Moore, Stephen P ^a   O'Brien, Peter ^a   Gilday, John ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 [3,5 BIS(TRIFLUOROMETHYL)BENZYLOXY] 2 PHENYLPIPERIDINE; N BOC PYRROLIDINE; N-BOC-PYRROLIDINE; NEUROKININ 1 RECEPTOR; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

MOLECULAR STRUCTURE; PIPERIDINES; PYRROLIDINES; RECEPTORS, NEUROKININ-1; STEREOISOMERISM;

EID: 65549120332     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900366m     Document Type: Article

References (58)

1. (a) Liao, Y. F.; Lal, A.; Moremen, K. W. J. Biol. Chem. 1996, 271, 28348.
2. (b) Elbein, A. D.; Solf, R.; Dorling, P. R.; Vosbeck, K. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 7393.
3. (c) Goss, P. E.; Baker, M. A.; Carver, J. P.; Dennis, J. W. Clin. Cancer. Res. 1995, 1, 935.
4. (a) Jang, C. S.; Fu, F. Y.; Wang, C. Y.; Huang, K. C.; Lu, G.; Thou, T. C. Science 1946, 103, 59.
5. (b) Chou, T.-Q.; Fu, F. Y.; Kao, Y. S. J.Am. Chem. Soc. 1948, 70, 1765.
6. (c) Frederick, A. K.; Spencer, C. F.; Folkers, K. J. Am. Chem. Soc. 1948, 70, 2091.
7. Harrison, T.; Williams, B. J.; Swain, C. J.; Ball, R. G. Bioorg. Med. Chem. Lett. 1994, 4, 2545.
8. For the most recent syntheses of (-)-swainsonine, see: (a) Shi, G.- F.; Li, J.-Q.; Jiang, X.-P.; Cheng, Y. Tetrahedron 2008, 64, 5005.
9. (b) Sharma, P. K.; Shah, R. N.; Carver, J. P. Org. Process Res Dev. 2008, 12, 831.
10. (c) Guo, H.; O'Doherty, G. Tetrahedron 2008, 64, 304.
11. (d) Déchamps, I.; Gomez Pardo, D.; Cossy, J. Tetrahedron 2007, 63, 9082.
12. (e) Ceccon, J.; Greene, A. E.; Poisson, J.-F. Org. Lett. 2006, 8, 4739.
13. For syntheses of (+)-febrifugine, see: (a) Sieng, B.; Lozano Ventura, O.; Bellosta, V.; Cossy, J. Synlett 2008, 1216.
14. (b) Ashoorzadeh, A.; Caprio, V. Synlett 2005, 346.
15. (c) Katoh, M.; Matsune, R.; Nagase, H.; Honda, T. Tetrahedron Lett. 2004, 45, 6221.
16. (d) Huang, P.-Q.; Wei, B.-G.; Ruan, Y.-P. Synlett 2003, 1663.
17. (e) Ooi, H.; Urushibara, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2001, 3, 953.
18. (f) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
19. (g) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Harayama, T. Chem. Commun. 2000, 1643.
20. (h) Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175.
21. For syntheses of (+)-L-733,060, see: (a) Liu, R.-H.; Fang, K.; Wang, B.; Xu, M.-H.; Lin, G.-Q. J. Org. Chem. 2008, 73, 3307.
22. (b) Emmanuvel, L.; Sudalai, A. Tetrahedron Lett. 2008, 49, 5736.
23. (c) Cherian, S. K.; Kumar, P. Tetrahedron: Asymmetry 2007, 18, 982.
24. (d) Oshitari, T.; Mandai, T. Synlett 2006, 3395.
25. (e) Kandula, S. R. V.; Kumar, P. Tetrahedron: Asymmetry 2005, 16, 3579.
26. (f) Yoon, Y.-J.; Joo, J.-E.; Lee, K.-Y.; Kim, Y.-H.; Oh, C.-Y.; Ham, W.-H. Tetrahedron Lett. 2005, 46, 739.
27. (g) Huang, P.-Q.; Liu, L.-X.; Wei, B.-G.; Ruan, Y.-P. Org. Lett. 2003, 5, 1927.
28. (h) Bhaskar, G.; Rao, B. V. Tetrahedron Lett. 2003, 44, 915. For synthesis of (-)-L-733,060, see:
29. (i) Takahashi, K.; Nakano, H.; Fujita, R. Tetrahedron Lett. 2005, 46, 8927.
30. Fuson, R. C.; Zirkle, C. L. J. Am. Chem. Soc. 1948, 70, 2760.
31. Cossy, J.; Dumas, C.; Michel, P.; Gomez Pardo, D. Tetrahedron Lett. 1995, 36, 549.
32. For selected examples, see: (a) Calvez, O.; Chiaroni, A.; Langlois, N. Tetrahedron Lett. 1998, 39, 9447.
33. (b) Cossy, J.; Dumas, C.; Gomez Pardo, D. Eur. J. Org. Chem. 1999, 1693.
34. (c) Cossy, J.; Mirguet, O.; Gomez Pardo, D.; Desmurs, J.-R. Tetrahedron Lett. 2001, 42, 5705.
35. (d) Lee, J.; Hoang, T.; Lewis, S.; Weissm an, S. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 2001, 42, 6223.
36. (e) Dechamps, I.; Gomez Pardo, D.; Cossy, J. Synlett 2007, 263.
37. (f) Drouillat, B.; Couty, F.; David, O.; Evano, G.; Marrot, J. Synlett 2008, 1345.
38. (g) Durrat, F; Vargas Sanchez, M.; Couty, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2008, 3286.
39. (a) Dearden, M. J.; Firkin, C. R.; Hermet, J.-P. R.; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870.
40. (b) Dearden, M. J.; McGrath, M. J.; O'Brien, P. J. Org. Chem. 2004, 69, 5789.
41. (c) Dixon, A. J.; McGrath, M. J.; O'Brien, P. Org. Synth. 2006, 83, 141.
42. (d) O'Brien, P. Chem. Commun. 2008, 655.
43. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
44. (a) McGrath, M. J.; O'Brien, P. J. Am. Chem. Soc. 2005, 127, 16378.
45. (b) McGrath, M. J.; Bilke, J. L.; O'Brien, P. Chem. Commun. 2006, 2607.
46. (c) Bilke, J. L.; O'Brien, P. J. Org. Chem. 2008, 73, 6452.
47. For selected examples on the use of n-BuLi/LiDMAE in pyridine lithiation, see: (a) Gros, P.; Fort, Y.; Queguiner, G.; Caubère, P. Tetrahedron Lett. 1995, 36, 4791.
48. (b) Gros, P.; Fort, Y.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1997, 3071.
49. (c) Gros, P.; Fort, Y. Eur. J. Org. Chem. 2002, 3375.
50. (d) Gros, P. C.; Doudouh, A.; Woltermann, C. Chem. Commun. 2006, 2673.
51. 1H NMR spectroscopy).
52. Stead, D.; O'Brien, P.; Sanderson, A. Org. Lett. 2008, 10, 1409.
53. We are aware of only one example of the addition of a lithiated N-Boc pyrrolidine to an aldehyde: Majewski, M.; Shao, J.; Nelson, K.; Nowak, P.; Irvine, N. M. Tetrahedron Lett. 1998, 39, 6787.
54. CCDC 696161 (anti-8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at http://www.ccdc.cam.ac.uk/ data-request/cif.
55. Kise, N.; Urai, T.; Yoshida, J.-i. Tetrahedron: Asymmetry 1998, 9, 3125.
56. Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945.
57. Basu, A.; Thayumanavan, S. Angew. Chem., Int. Ed. 2002, 41, 716.
58. For a similar effect with O-alkyl carbamates, see: Tomooka, K.; Shimizu, H.; Nakai, T. J. Organomet. Chem. 2001, 624, 364.