Catalytic enantioselective aziridination of alkenes using chiral dirhodium(II) carboxylates

Heterocycles

Volumn 72, Issue , 2007, Pages 709-721

  Yamawaki, Minoru ^a   Tanaka, Masahiko ^a   Abe, Takumi ^a   Anada, Masahiro ^a   Hashimoto, Shunichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547843706     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-07-s(k)63     Document Type: Article

References (68)

1. For recent reviews on aziridination of alkenes with iminoiodinanes, see. Müller P. In: Doyle M.P. (Ed). Advances in Catalytic Processes Volume 2 (1997), JAI Press, Greenwich 113
2. Chapter 17. Jacobsen E.N. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Berlin
3. Chapter 6134. Katsuki T. Catalytic Asymmetric Synthesis. In: Ojima I. (Ed) (2000), Wiley-VCH, New York
4. Dauban P., and Dodd R.H. Synlett (2003) 1571
5. Chapter 12. Doyle M.P. Reactive Intermediate Chemistry. In: Moss R.A., Platz M.S., and Jones Jr. M. (Eds) (2004), John Wiley & Sons, Hoboken
6. Müller P., and Fruit C. Chem. Rev. 103 (2003) 2905
7. Evans D.A., Woerpel K.A., Hinman M.M., and Faul M.M. J. Am. Chem. Soc. 113 (1991) 726
8. Lowenthal R.E., and Masamune S. Tetrahedron Lett. 32 (1991) 7373
9. Evans D.A., Faul M.M., Bilodeau M.T., Anderson B.A., and Barnes D.M. J. Am. Chem. Soc. 115 (1993) 5328
10. Södergren M.J., Alonso D.A., and Andersson P.G. Tetrahedron: Asymmetry 8 (1997) 3563
11. Dauban P., Saniére L., Tarrade A., and Dodd R.H. J. Am. Chem. Soc. 123 (2001) 7707
12. Xu J., Ma L., and Jiao P. Chem. Commun. (2004) 1616
13. Kwong H.-L., Liu D., Chan K.-Y., Lee C.-S., Huang K.-H., and Che C.-M. Tetrahedron Lett. 45 (2004) 3965
14. Ma L., Jiao P., Zhang Q., and Xu J. Tetrahedron: Asymmetry 16 (2005) 3718
15. Li Z., Conser K.R., and Jacobsen E.N. J. Am. Chem. Soc. 115 (1993) 5326
16. Li Z., Quan R.W., and Jacobsen E.N. J. Am. Chem. Soc. 117 (1995) 5889
17. Cho D.-J., Jeon S.-J., Kim H.-S., Cho C.-S., Shim S.-C., and Kim T.-J. Tetrahedron: Asymmetry 10 (1999) 3833
18. Sanders C.J., Gillespie K.M., Bell D., and Scott P. J. Am. Chem. Soc. 122 (2000) 7132
19. Gillespie K.M., Crust E.J., Deeth R.J., and Scott P. Chem. Commun. 785 (2001)
20. Shi M., Wang C.-J., and Chan A.S.C. Tetrahedron: Asymmetry 12 (2001) 3105
21. Gillespie K.M., Sanders C.J., O'Shaughnessy P., Westmoreland I., Thickitt C.P., and Scott P. J. Org. Chem. 67 (2002) 3450
22. Suga H., Kakehi A., Ito S., Ibata T., Fudo T., Watanabe Y., and Kinoshita Y. Bull. Chem. Soc. Jpn. 76 (2003) 189
23. Wang X., and Ding K. Chem. Eur. J. 12 (2006) 4568
24. Tanner D., Andersson P.G., Harden A., and Somfai P. Tetrahedron Lett. 35 (1994) 4631
25. Llewellyn D.B., Adamson D., and Arndtsen B.A. Org. Lett. 2 (2000) 4165
26. Lam T.C.H., Mak W.-L., Wong W.-L., Kwong H.-L., Sung H.H.Y., Lo S.M.F., Williams I.D., and Leung W.-H. Organometallics 23 (2004) 1247
27. Noda K., Hosoya N., Irie R., Ito Y., and Katsuki T. Synlett (1993) 469
28. Nishikori H., and Katsuki T. Tetrahedron Lett. 37 (1996) 9245
29. Lai T.-S., Kwong H.-L., Che C.-M., and Peng S.-M. Chem. Commun. (1997) 2373
30. Simonato J.-P., Pécaut J., Scheidt W.R., and Marchon J.-C. Chem. Commun. (1999) 989
31. Liang J.-L., Huang J.-S., Yu X.-Q., Zhu N., and Che C.-M. Chem. Eur. J. 8 (2002) 1563
32. Liang J.-L., Yu X.-Q., and Che C.-M. Chem. Commun. (2002) 124
33. Chiral ruthenium(II) salen complexes of Katsuki have recently been reported to catalyze the aziridination of various terminal conjugated alkenes using sulfonyl azides as a nitrene precursor with excellent enantioselectivity and turnover number. Omura K., Murakami M., Uchida T., Irie R., and Katsuki T. Chem. Lett. 32 (2003) 354
34. Omura K., Uchida T., Irie R., and Katsuki T. Chem. Commun. (2004) 2060
35. Katsuki T. Chem. Lett. 34 (2005) 1304
36. Kawabata H., Omura K., and Katsuki T. Tetrahedron Lett. 47 (2006) 1571
37. Breslow R., and Gellman S.H. J. Am. Chem. Soc. 105 (1983) 6728
38. Evans D.A., Faul M.M., and Bilodeau M.T. J. Org. Chem. 56 (1991) 6744
39. Evans D.A., Faul M.M., and Bilodeau M.T. J. Am. Chem. Soc. 116 (1994) 2742
40. Müller P., Baud C., and Jacquier Y. Tetrahedron 52 (1996) 1543
41. Müller P., Baud C., and Jacquier Y. Can. J. Chem. 76 (1998) 738
42. Liang J.-L., Yuan S.-X., Chan P.W.H., and Che C.-M. Org. Lett. 4 (2002) 4507
43. Liang J.-L., Yuan S.-X., Chan P.W.H., and Che C.-M. Tetrahedron Lett. 44 (2003) 5917
44. Fruit C., and Miller P. Tetrahedron: Asymmetry 15 (2004) 1019
45. Hayes C.J., Beavis P.W., and Humphries L.A. Chem. Commun. (2006) 4501
46. Yamawaki M., Tsutsui H., Kitagaki S., Anada M., and Hashimoto S. Tetrahedron Lett. 43 (2002) 9561
47. Watanabe N., Ogawa T., Ohtake Y., Ikegami S., and Hashimoto S. Synlett (1996) 85
48. Anada M., and Hashimoto S. Tetrahedron Lett. 39 (1998) 79
49. Anada M., and Hashimoto S. Tetrahedron Lett. 39 (1998) 9063
50. Kitagaki S., Yasugahira M., Anada M., Nakajima M., and Hashimoto S. Tetrahedron Lett. 41 (2000) 5931
51. Takahashi T., Tsutsui H., Tamura M., Kitagaki S., Nakajima M., and Hashimoto S. Chem. Commun. (2001) 1604
52. Kitagaki S., Yanamoto Y., Tsutsui H., Anada M., Nakajima M., and Hashimoto S. Tetrahedron Lett. 42 (2001) 6361
53. Tsutsui H., Matsuura M., Makino K., Nakamura S., Nakajima M., Kitagaki S., and Hashimoto S. Isr. J. Chem. 41 (2001) 283
54. Saito H., Oishi H., Kitagaki S., Nakamura S., Anada M., and Hashimoto S. Org. Lett. 4 (2002) 3887
55. Minami K., Saito H., Tsutsui H., Nambu H., Anada M., and Hashimoto S. Adv. Synth. Catal. 347 (2005) 1483
56. Natori Y., Anada M., Nakamura S., Nambu H., and Hashimoto S. Heterocycles 70 (2006) 635
57. 4, see:. Tsutsui H., Abe T., Nakamura S., Anada M., and Hashimoto S. Chem. Pharm. Bull. 53 (2005) 1366
58. Yamawaki M., Kitagaki S., Anada M., and Hashimoto S. Heterocycles 69 (2006) 527
59. FarrAs J., Ginesta X., Sutton P.W., Taltavull J., Egeler F., Romea P., Urpí F., and Vilarrasa J. Tetrahedron 57 (2001) 7665
60. 2, 0 °C) gave a complex mixture of products.
61. Tsutsui H., Yamaguchi Y., Kitagaki S., Nakamura S., Anada M., and Hashimoto S. Tetrahedron: Asymmetry 14 (2003) 817
62. Nägeli I., Baud C., Bernardinelli G., Jacquier Y., Moran M., and Müller P. Helv. Chim. Acta 80 (1997) 1087
63. Yamada Y., Yamamoto T., and Okawara M. Chem. Lett. 4 (1975) 361
64. Södergren M.J., Alonso D.A., Bedekar A.V., and Andersson P.G. Tetrahedron Lett. 38 (1997) 6897
65. Kim S.K., and Jacobsen E.N. Angew. Chem. Int. Ed. 43 (2004) 3952
66. Leung S.K.-Y., Tsui W.-M., Huang J.-S., Che C.-M., Liang J.-L., and Zhu N. J. Am. Chem. Soc. 127 (2005) 16629
67. Alonso D.A., and Andersson P.G. J. Org. Chem. 63 (1998) 9455
68. Keaney G.F., and Wood J.L. Tetrahedron Lett. 46 (2005) 4031