Ir-catalyzed allylic amination/ring-closing metathesis: A new route to enantioselective synthesis of cyclic β-amino alcohol derivatives

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7443-7446

  Jun, Hee Lee ^b   Shin, Seunghoon ^c   Kang, Jahyo ^b   Lee, Sang Gi ^a  

^a Ewha Womans University   (South Korea)

^b Sogang University   (South Korea)

^c Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYST ACTIVITY; CHIRALITY; DERIVATIVES; IRIDIUM COMPOUNDS; LIGANDS;

AMINO ALCOHOLS; CHIRAL LIGANDS; METATHESIS; PHOSPHORAMIDITE;

BENZENE;

ALCOHOL DERIVATIVE; ALLYL COMPOUND; AMINOALCOHOL; BENZYLAMINE; BETA AMINO ACID; CARBONIC ACID DERIVATIVE; IRIDIUM; PHOSPHORAMIDOUS ACID;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS;

ALLYL COMPOUNDS; AMINATION; AMINO ALCOHOLS; CATALYSIS; CYCLIZATION; IRIDIUM; STEREOISOMERISM;

EID: 34548802917     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070998h     Document Type: Article

References (52)

1. (a) Lovell, P. J.; Bromidge, S. M.; Dabbs, S.; Duckworth, D. M.; Forbes, I. T.; Jennings, A. J.; King, F. D.; Middlemiss, D. N.; Rahman, S. K.; Saunders, D. V.; Collin, L. L.; Hagan, J. J.; Riley, G. J.; Thomas, D. R. J. Med. Chem. 2000, 43, 342.
2. (b) Cardillo, G.; Gentilucci, L.; Qasem, A. R.; Sgarzi, F.; Spampinato, S. J. Med. Chem. 2002, 45, 2571.
3. (c) Vernier, J.-M.; El-Abdellaoui, H.; Holsenback, H.; Cosford, N. D. P.; Bleicher, L.; Barker, G.; Bontempi, B.; Chavez-Noriega, L.; Menzaghi, F.; Rao, T. S.; Reid, R.; Sacaan, A. I.; Suto, C.; Washburn, M.; Lloyd, G. K.; McDonald, I. A. J. Med. Chem. 1999, 42, 1684.
4. (d) Stapper, C.; Blechert, S. J. Org. Chem. 2002, 67, 6456.
5. (e) Deng, X.; Mani, N. S. Tetrahedron: Asymmetry 2005, 16, 661.
6. (f) Gautiér-Lefevre, I.; Behr, J. B.; Guillérn, G.; Muzard, M. Eur. J. Med. Chem. 2005, 40, 1255.
7. (g) Ayad, T.; Faugeroux, V.; Genisson, Y.; Andre, C.; Baltas, M.; Gorrichon, L. J. Org. Chem. 2004, 69, 8775.
8. (h) Nolen, E. G.; Kurish, A. J.; Potter, J. M.; Donahue, L. A.; Orland, M. D. Org. Lett. 2005, 7, 3383.
9. (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
10. (b) Katritzky, A. R.; Zhang, S.; Fang, Y. Org. Lett. 2000, 2, 3789.
11. (c) Katritzky, A. R.; Zhang, S.; Hussein, A. H. M.; Fang, Y.; Steel, P. J. J. Org. Chem. 2001, 66, 5606.
12. (d) Kowalski, C. J.; Reddy, R. E. J. Org. Chem. 1992, 57, 7194.
13. (e) Gray, D.; Concellón, C.; Gallagher, T. J. Org. Chem. 2004, 69, 4849.
14. (a) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
15. (b) Sewald, N. Angew. Chem., Int. Ed. 2003, 42, 5794.
16. (c) Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253.
17. (d) Perlmutter, P.; Rose, M.; Vounatsos, F. Eur. J. Org. Chem. 2003, 756.
18. (e) Lesma, G.; Danieli, B.; Sacchetti, A.; Silvani, A. J. Org. Chem. 2006, 71, 3317.
19. (a) Lee, S.-g.; Zhang, Y. J. Org. Lett. 2002, 4, 2429.
20. (b) Zhang, Y. J.; Park, J. H.; Lee, S.-g. Tetrahedron: Asymmetry 2004, 15, 2209.
21. (a) Battels, B.; Helmchen, G. Chem. Commun. 1999, 741.
22. (b) Barters, B.; García-Yebra, C.; Rominger, F.; Helmchen, G. Eur. J. Inorg. Chem. 2002, 2569.
23. (c) Lipowsky, G.; Miller, N.; Helmchen, G. Angew. Chem., Int. Ed. 2004, 116, 4595.
24. (d) Alexakis, A.; Polet, D. Org. Lett. 2004, 6, 3529.
25. (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164.
26. (b) Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14272.
27. (c) Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 116.
28. (d) Welter, C.; Koch, O.; Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 896.
29. (e) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426.
30. (f) Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797.
31. (g) Leitner, A.; Shu, C.; Hartwig, J. F. Org. Lett. 2005, 7, 1093.
32. (h) Welter, C.; Dahnz, A.; Brunner, B.; Streiff, S.; Dübon, P.; Helmchen, G. Org. Lett. 2005, 7, 1239.
33. (i) Polet, D.; Alexakis, A. Org. Lett. 2005, 7, 1621.
34. (j) Weihofen, R.; Dahnz, A.; Tverskoy, O.; Helmchen, G. Chem. Commun. 2005, 3541.
35. (k) Weihofen, R.; Tverskoy, O.; Helmchen, G. Angew. Chem., Int. Ed. 2006, 45, 5546.
36. (a) Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
37. (b) Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794.
38. Streiff, S.; Welter, C.; Schelwies, M; Lipowsky, G.; Miller, N.; Helmchen, G. Chem. Commun. 2005, 2957.
39. (a) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761.
40. (b) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929.
41. Wright, D. L.; Schulte, J. P., II; Page, M. A. Org. Lett. 2000, 2, 1847.
42. Takeuchi, R.; Ue, N.; Tanabe, K.; Yamashita, K.; Shiga, N. J. Am. Chem. Soc. 2001, 123, 9525.
43. (a) Azzena, F.; Calvani, F.; Crotti, P.; Gardelli, C.; Macchia, F.; Pineschi, M. Tetrahedron 1995, 51, 10601.
44. (b) Bouzide, A.; Sauvé, G. Tetrahedron Lett. 1997, 38, 5945.
45. (c) Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
46. (a) de Vries, A. H. M.; Meetsma, A.; Feringa, B. L. Angew. Chem., Int. Ed. 1996, 35, 2374.
47. (b) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. 1997, 36, 2620.
48. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
49. (b) Furstner, A.; Langmann, K. J. J. Am. Chem. Soc. 1997, 64, 5321.
50. (c) Yang, Q.; Xiao, W. J.; Yu, Z. Org. Lett. 2005, 7, 871.
51. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
52. (b) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.