Concise synthesis of α-trisubstituted amines from ketones using n -methoxyamines

Organic Letters

Volumn 14, Issue 8, 2012, Pages 2098-2101

  Kurosaki, Yusuke ^a   Shirokane, Kenji ^a   Oishi, Takeshi ^a   Sato, Takaaki ^a   Chida, Noritaka ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; KETONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINES; CATALYSIS; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84860161791     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300622r     Document Type: Article

References (53)

1. Kuramoto, M.; Tong, C.; Yamada, K.; Chiba, T.; Hayashi, Y.; Uemura, D. Tetrahedron Lett. 1996, 37, 3867-3870
2. Arimoto, H.; Hayakawa, I.; Kuramoto, M.; Uemura, D. Tetrahedron Lett. 1998, 39, 861-862
3. Clive, D. L. J.; Yu, M.; Wang, J.; Yeh, V. S. C.; Kang, S. Chem. Rev. 2005, 105, 4483-4514
4. Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37-44
5. Daly, J. W.; Karle, I.; Myers, C. W.; Tokuyama, T.; Waters, J. A.; Witkop, B. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1870-1875
6. Sinclair, A.; Stockman, R. A. Nat. Prod. Rep. 2007, 24, 298-326
7. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995
8. Sugiura, M.; Kobayashi, S. Angew. Chem., Int. Ed. 2005, 44, 5176-5186
9. Shibasaki, M.; Kanai, M. Org. Biomol. Chem. 2007, 5, 2027-2039
10. Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853-2873
11. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600-3740
12. Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626-2704
13. Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N. Angew. Chem., Int. Ed. 2010, 49, 6369-6372
14. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Am. Chem. Soc. 1985, 107, 5534-5535
15. Vincent, G.; Guillot, R.; Kouklovsky, C. Angew. Chem., Int. Ed. 2011, 50, 1350-1353
16. Hardegger, B.; Shatzmiller, S. Helv. Chim. Acta 1976, 59, 2765-2767
17. Plate, R.; van Hout, R. H. M.; Behm, H.; Ottenheijm, H. C. J. J. Org. Chem. 1987, 52, 555-560
18. Padwa, A.; Dean, D. C. J. Org. Chem. 1990, 55, 405-406
19. Hermkens, P. H. H.; van Maarseveen, J. H.; Cobben, P. L. H. M.; Ottenheijm, H. C. J.; Kruse, C. G.; Scheeren, H. W. Tetrahedron 1990, 46, 833-846
20. Tiecco, M.; Testaferri, L.; Tingoli, M.; Bagnoli, L. J. Chem. Soc., Chem. Commun. 1995, 235-236
21. McMills, M. C.; Wright, D. L.; Zubkowski, J. D.; Valente, E. J. Tetrahedron Lett. 1996, 37, 7205-7208
22. Grigg, R.; Rankovic, Z.; Thoroughgood, M. Tetrahedron 2000, 56, 8025-8032
23. Yamashita, T.; Kawai, N.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2005, 127, 15038-15039
24. Dondas, H. A.; Grigg, R.; Markandu, J.; Perrior, T.; Suzuki, T.; Thibault, S.; Thomas, W. A.; Thornton-Pett, M. Tetrahedron 2002, 58, 161-173
25. Peng, Z.; Song, J.; Liao, W.; Ma, R.; Chen, S.-H.; Li, G.; Ando, R. Lett. Org. Chem. 2006, 3, 455-458
26. Nemoto, H.; Ma, R.; Kawamura, T.; Kamiya, M.; Shibuya, M. J. Org. Chem. 2006, 71, 6038-6043
27. Zheng, X.; Wang, X.; Chang, J.; Zhao, K. Synlett 2006, 3277-3283
28. Nemoto, H.; Ma, R.; Moriguchi, H.; Kawamura, T.; Kamiya, M.; Shibuya, M. J. Org. Chem. 2007, 72, 9850-9853
29. Jackson, S. K.; Karadeolian, A.; Driega, A. B.; Kerr, M. A. J. Am. Chem. Soc. 2008, 130, 4196-4201
30. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946
31. Bloch, R. Chem. Rev. 1998, 98, 1407-1438
32. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293
33. Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595-614
34. Bonjoch, J.; Diaba, F.; Puigbó, G.; Solé, D.; Segarra, V.; Santamaría, L.; Beleta, J.; Ryder, H.; Palacios, J.-M. Bioorg. Med. Chem. 1999, 7, 2891-2897
35. Wright, D. L.; Schulte, J. P., II; Page, M. A. Org. Lett. 2000, 2, 1847-1850
36. Varlamov, A.; Kouznetsov, V.; Zubkov, F.; Chernyshev, A.; Shurupova, O.; Méndez, L. Y. V.; Rodríguez, A. P.; Castro, J. R.; Rosas-Romero, A. J. Synthesis 2002, 771-783
37. Dhudshia, B.; Tiburcio, J.; Thadani, A. N. Chem. Commun. 2005, 5551-5553
38. Kropf, J. E.; Meigh, I. C.; Bebbington, M. W. P.; Weinreb, S. M. J. Org. Chem. 2006, 71, 2046-2055
39. Kaden, S.; Reissig, H.-U. Org. Lett. 2006, 8, 4763-4766
40. Prusov., E.; Maier, M. E. Tetrahedron 2007, 63, 10486-10496
41. Miyabe, H.; Ueda, M.; Naito, T. Synlett 2004, 1140-1157
42. Cho, D. H.; Jang, D. O. Chem. Commun. 2006, 5045-5047
43. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094
44. Ohfune, Y.; Shinada, T. Bull. Chem. Soc. Jpn. 2003, 76, 1115-1129
45. Gröger, H. Chem. Rev. 2003, 103, 2795-2827
46. Vilaivan, T.; Bhanthumnavin, W.; Sritana-Anant, Y. Curr. Org. Chem. 2005, 9, 1315-1392
47. Friestad, G. K.; Mathies, A. K. Tetrahedron 2007, 63, 2541-2569
48. Monfray, J.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Tetrahedron: Asymmetry 2005, 16, 1025-1034
49. Amorde, S. M.; Jewett, I. T.; Martin, S. F. Tetrahedron 2009, 65, 3222-3231
50. The structure of 29 was determined by single-crystal X-ray analysis (CCDC 864124). These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
51. Tufariello, J. J.; Mullen, G. B.; Tegeler, J. J.; Trybulski, E. J.; Wong, S. C.; Ali, S. A. J. Am. Chem. Soc. 1979, 101, 2435-2442
52. Ali, S. A.; Wazeer, M. I. M. Tetrahedron Lett. 1993, 34, 137-140
53. Nagasawa, K.; Georgieva, A.; Koshino, H.; Nakata, T.; Kita, T.; Hashimoto, Y. Org. Lett. 2002, 4, 177-180