Lewis acid assisted ring-closing metathesis of chiral diallylamines: An efficient approach to enantiopure pyrrolidine derivatives

Organic Letters

Volumn 7, Issue 5, 2005, Pages 871-874

  Yang, Qian ^a   Xiao, Wen Jing ^a   Yu, Zhengkun ^b  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINE; LEWIS ACID; PYRROLIDINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYST; RING CLOSING METATHESIS;

EID: 15044355873     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047356q     Document Type: Article

References (50)

1. (a) Ung, T.; Hejl, A.; Grubbs, R. H.; Schrodi, Y. Organometallics 2004, 23, 5399.
2. (b) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
3. (c) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973.
4. (d) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
5. For recent reviews, see: (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239. (b) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2. (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
6. For recent reviews, see: (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239. (b) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2. (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
7. For recent reviews, see: (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239. (b) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2. (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
8. For recent reviews, see: (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239. (b) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2. (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
9. For recent reviews, see: (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239. (b) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2. (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
10. For recent reviews, see: (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239. (b) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2. (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
11. (a) Brouwer, A. J.; Liskamp, R. M. J. J. Org. Chem. 2004, 69, 3662.
12. (b) Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2004, 126, 15074.
13. (c) Kim, Y. J.; Lee, D. Org. Lett. 2004, 62, 4351.
14. (e) Chen, Y.; Zhang, H.; Nan, F. J. Comb. Chem. 2004, 6, 684.
15. (f) Chen, X.; Wiemer, D. F. J. Org. Chem. 2003, 68, 6597.
16. (g) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390.
17. (h) Yao, Q. Org. Lett. 2002, 4, 427.
18. (j) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Org. Lett. 2001, 3, 3939.
19. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem. 2000, 65, 4721.
20. (l) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 5426.
21. (m) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
22. (a) Dieltiens, N.; Stevens, C. V.; Vos, D. D.; Allaert, B.; Drozdzak, R.; Verpoort, F. Tetrahedron Lett. 2004, 45, 8995.
23. (b) Clercq, B. D.; Verpoort, F. Tetrahedron Lett. 2001, 42, 8959.
24. (c) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517.
25. (d) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204.
26. (a) Evans, P.; Grigg, R.; Ramzan, M. I.; Sridharan, V.; York, M. Tetrahedron Lett. 1999, 40, 3021.
27. (b) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082.
28. (c) Williams, R. M.; Liu, J. J. Org. Chem. 1998, 63, 2130.
29. (d) Furstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2466.
30. (e) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855.
31. (f) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
32. An example of RCM of ortho-halo and ortho-vinyl anilines, see: Evans, P.; Grigg, R.; Monteith, M. Tetrahedron Lett. 1999, 40, 5247.
33. Hoekstra, W. J.; Maryanoff, B. E.; Damiano, B. P.; Andrade-Gordon, P.; Cohen, J. H.; Costanzo, M. J.; Haertlein, B. J.; Hecker, L. R.; Hulshizer, B. L.; Kauffman, J. A.; Keane, P.; McComsey, D. F.; Mitchell, J. A.; Scott, L.; Shah, R. D.; Yabut, S. C. J. Med. Chem. 1999, 42, 5254.
34. Wang, C.-L. J.; Taylor, T. L.; Mical, A. J.; Spitz, S.; Reilly, T. M. Tetrahedron Lett. 1992, 33, 667.
35. (a) Fallorni, M.; Porcheddu, A.; Giacomello, G. Tetrahedron: Asymmetry 1997, 8, 1633.
36. (b) Hamilton, G. S.; Huang, Z.; Yang, X.-J.; Patch, R. J.; Naranyan, B. A.; Ferkany, J. W. J. Org. Chem. 1993, 58, 7262.
37. (a) O'Hagan, D.Nat. Prod. Rep. 2000, 17, 435.
38. (b) O'Hagan, D. Nat. Prod. Rep. 1997, 14, 637.
39. (c) Morgans, D. J.; Stork, G. Tetrahedron Lett. 1979, 20, 1959.
40. Xiao, W.-J.; Ung, T. A.; Pederson, R. L. The 6th National Conference on Phosphorus Chemistry & Chemical Engineering, Wuhan, China, Sept., 2003; p 136.
41. (a) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769.
42. (b) Mancilla, T.; Carrillo, L.; Zamudio-Rivera, L. S.; Beltran, H. I.; Farfan, N. Org. Prep. Proced. Int. 2001, 33, 341.
43. (c) Mancilla, T.; Carrillo, L.; Zamudio-Rivera, L. S.; Beltran, H. I.; Farfan, N. Org. Prep. Proced. Int. 2002, 34, 87.
44. (d) Majumdar, K. C.; Kundu, A. K.; Chatterjee, P. J. Chem. Res., Synop. 1996, 460.
45. Yang, C.; Murray, W. V.; Wilson, L. J. Tetrahedron Lett. 2003, 44, 1783.
46. Encyclopedia of Reagents for Organic Synthesis: Paquette, L. A., Ed.; Wiley: New York, 1995.
47. (a) Furstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
48. (b) Wipf, P.; Weiner, W. S. J. Org. Chem. 1999, 64, 5321.
49. See the HPLC analysis of 13 and its enantiomer in Supporting Information.
50. Grubbs and co-workers have carried out the RCM reaction of the corresponding hydrochloride salt of 26 using 6b as the catalyst, affording 27 in 79% isolated yield after the treatment of NaOH. Please see ref 5f.