A highly stereoselective organocatalytic tandem aminoxylation/aza-Michael reaction for the synthesis of tetrahydro-1,2-oxazines

Organic Letters

Volumn 10, Issue 20, 2008, Pages 4585-4588

  Zhu, Di ^a   Lu, Min ^a   Chua, Pei Juan ^a   Tan, Bin ^a   Wang, Fei ^a   Yang, Xinhao ^a,b   Zhong, Guofu ^a  

^a Nanyang Technological University   (Singapore)

^b Alpha Building   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HETEROCYCLIC COMPOUND; HYDRAZINE; HYDRAZINE DERIVATIVE; HYDROGEN; OXAZINE DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINES; AZA COMPOUNDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HYDRAZINES; HYDROGEN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANIC CHEMISTRY PHENOMENA; OXAZINES; OXIDATION-REDUCTION; SOLVENTS;

EID: 57749101251     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801864c     Document Type: Article

References (60)

1. (a) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134.
2. (b) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962.
3. (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395.
4. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260.
5. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591.
6. (d) Momiyama, N.; Torii, H.; Saito, S.; Yamamoto, H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5374.
7. (e) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
8. (f) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
9. (g) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785.
10. (a) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677.
11. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
12. (c) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866.
13. (d) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842.
14. (e) List, B. J. Am. Chem. Soc. 2000, 122, 9336.
15. (a) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.
16. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737.
17. (a) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233.
18. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498.
19. (c) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.
20. (a) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685.
21. (b) List, B. J. Am. Chem. Soc. 2002, 124, 5656.
22. (a) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247.
23. (b) Brown, S. P.; Brochu. M. P.; Sinz, C. J.: MacMillan. D. W. C. J. Am. Chem. Soc. 2003, 125, 10808.
24. (c) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8243.
25. (d) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112.
26. (c) Bøgevig, A. M.; Sundeen, H.; Cordova. A. Angew. Chem., Int. Ed. 2004, 43, 1109.
27. (f) Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317.
28. (g) Cheong, P. H.-Y.; Houk, K. N. J. Am. Chem. Soc. 2004, 126, 13912.
29. (h) Iwamura, H.; Wells, D. H.. Jr.; Mathew, S. P.; Klussmann, M.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 16312.
30. (i) Zhong, G. Chem. Commun. 2004, 606.
31. (j) Zhong, G.; Yu, Y. Org. Lett. 2004, 6, 637.
32. (k) Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2005, 7, 1577.
33. (l) Kumarn, S.; Oelke, A. J.; Shaw, D. M.; Longhottom, D. A.; Ley, S. V. Org. Biomol. Chem. 2007, 5, 2678.
34. (m) Zhu, X.; Tanaka, F.; Hu, Y.; Heine, A.; Fuller, R.; Zhong, G.; Olson, A. J.; Lerner, R. A.; Barbas, C. F., III.; Wilson. I. A. J. Mol. Biol. 2004, 343, 1269.
35. (a) Uchida, I.; Takase, S.; Kayakiri, H.; Kiyoto, S.; Hashimoto, M. J. Am. Chem. Soc. 1987, 109, 4108.
36. (b) Terano, H.; Takase, S.; Hosoda, J.; Kohsaka, M. J. Antibiot. 1989, 42, 145.
37. (c) Yu, Q.-S.; Zhu, X.; Holloway, H. W.; Whittaker, N. F.; Brossi, A.; Greig, N. H. J. Med. Chem. 2002, 45, 3684.
38. (d) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229.
39. (e) Judd, T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2002, 41, 4683.
40. (f) Suzuki, M.; Kambe, J.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2002, 41, 4686.
41. (a) Pulz, R.; Al-Harrasi, A.; Reissig, H.-U. Org. Lett. 2002, 4, 2353.
42. (b) Tishkov, A. A.; Reissig, H.-U.; Ioffe, S. L. Synlett 2002, 863.
43. (c) Buchholz, M.; Reissig, H.-U. Eur. J. Org. Chem. 2003, 3524.
44. (d) Al-Harrasi, A.; Reissig, H.-U. Angew. Chem., Int. Ed. 2005, 44, 6227.
45. (e) Carson, C. A.; Kerr, M. A. Angew. Chem. Int. Ed. 2006, 45, 6560.
46. Palomo, C; Vera, S.; Velilla, I.; Mielgo, A. Angew. Chem., Int. Ed. 2007, 46, 8054.
47. (a) Momiyama, N.; Yamamoto, H. Org. Lett. 2002, 4, 3579.
48. (b) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360.
49. (c) Guo, H.-M.; Cheng, L.; Cun, L. F.; Gong, L.-Z.; Mi, A. Q.; Jiang, Y.-Z. Chem. Commun. 2006, 429.
50. (d) Kano, T.; Ueda, M.; Takai, J.; Maruoka, K. J. Am. Chem. Soc. 2006, 126, 5360.
51. Wabnitz, T. C.; Saaby, S.; Jorgensen, K. A. Org. Biomol. Chem. 2004, 2, 828.
52. Enantioselective Synthesis of β-Amino Acids, 2nd ed.: Juaristi, E. C., Soloshonok, V. A., Eds.; Wiley-VCH Ltd.: New York, 2005.
53. (a) Fustero, S.; Jimenez, D.; Moscardo, J.; Catalan, S.; del Pozo, C. Org. Lett. 2007, 9, 5283.
54. (b) Ibrahem, I.; Rios, R.; Vesely, J.; Zhao, G.-L.; Cordova, A. Chem. Commun. 2007, 849.
55. (c) Vesely, H.; Ibrahem, I.; Zhao, G.-L.; Rios, R.; Cordova, A. Angew. Chem., Int. Ed. 2007, 46, 778.
56. (d) Sunden, H.: Rios, R.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Cordova, A. Adv. Synth. Catal. 2007, 349, 827.
57. (e) Vesely, J.; Ibrahem, I.; Riós, R.; Zhao, G.-L.; Xu, Y.; Cordova, A. Tetrahedron Lett. 2007, 48, 2193.
58. (f) Li, H.; Wang, J.; Xie, H.; Zu, L.; Jiang, W.; Duesler, E. N.; Wang, W. Org. Lett. 2007, 9, 965.
59. (g) Chen, Y. K.; Yoshida, M.; McMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328.
60. (h) Gerasyuto, A. I.; Hsung, R. P.; Sydorenko, N.; Slater, B. W. J. Org. Chem. 2005, 70, 4248.