Asymmetric imidation of organic selenides into selenimides

Journal of Organometallic Chemistry

Volumn 611, Issue 1-2, 2000, Pages 475-487

  Miyake, Yoshihiro ^a   Oda, Masamitsu ^a   Oyamada, Arihiro ^a   Takada, Hiroya ^a   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric imidation; Chloramine T trihydrate; Organic selenides; Organic selenimides; N (Tosyl)imino phenyliodinane

Indexed keywords

EID: 0001316917     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00488-5     Document Type: Article

References (52)

1. See for example: P. Metzner, A. Thuillier, Sulfur Reagents in Organic Synthesis, Academic Press, London, 1994.
2. (a) N. Komatsu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 58 (1993) 4529.
3. (b) N. Komatsu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 58 (1993) 7624.
4. (c) H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, Chem. Commun. (1996) 931.
5. (d) H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, C.P. Baird, T.J. Sparey, P.C. Taylor, J. Org. Chem. 62 (1997) 6512.
6. (e) H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, Phosphorus Sulfur Silicon Relat. Elements 120-121 (1997) 363.
7. (f) Y. Miyake, H. Takada, K. Ohe, S. Uemura, J. Chem. Soc. Perkin Trans. 1 (1998) 2373.
8. (a) T. Shimizu, N. Kamigata, Org. Prep. Proced. Int. 29 (1997) 603.
9. (b) F.A. Davis, R.T. Reddy, J. Org. Chem. 57 (1992) 2599.
10. (a) N. Komatsu, T. Murakami, Y. Nishibayashi, T. Sugita, S. Uemura, J. Org. Chem. 58 (1993) 3697.
11. (b) N. Komatsu, S. Matsunaga, T. Sugita, S. Uemura, J. Am. Chem. Soc. 115 (1993) 5847.
12. (c) Y. Nishibayashi, J.D. Singh, S. Fukuzawa, S. Uemura, J. Org. Chem. 60 (1995) 4114.
13. (a) V.P. Krasnov, V.I. Naddaka, V.I. Minkin, Zh. Org. Khim. 17 (1981) 445.
14. (b) V.P. Krasnov, V.I. Naddaka, V.I. Minkin, Chem. Abstr. 95 (1981) 42551x.
15. J. Zhang, N. Kurose, S. Saito, T. Takahashi, T. Koizumi, J. Synth. Org. Chem. Jpn. 57 (1999) 587.
16. (a) T. Shimizu, N. Seki, H. Taka, N. Kamigata, J. Org. Chem. 61 (1996) 6013.
17. (b) H. Taka, T. Shimizu, F. Iwasaki, M. Yasui, N. Kamigata, J. Org. Chem. 64 (1999) 7433.
18. Y. Nishibayashi, T. Chiba, K. Ohe, S. Uemura, J. Chem. Soc. Chem. Commun. (1995) 1243.
19. Preliminary communication of enantioselective imidation: H. Takada, M. Oda, Y. Miyake, K. Ohe, S. Uemura, Chem. Commun. (1998) 1557.
20. Toluene has already been revealed to be the solvent of choice for asymmetric sulfimidation of organic sulfides, refs. [2c-f].
21. The excess selenide was employed (2.0 equivalents) and TsN=IPh served as the limiting reagent.
22. S. Tamagaki, S. Oae, K. Sasaki, Tetrahedron Lett. (1975) 649.
23. (a) F.A. Davis, R.T. Reddy, Tetrahedron 41 (1985) 4747.
24. (b) K.B. Sharpless, M.W. Young, R.F. Lauer, Tetrahedron Lett. (1973) 1979.
25. (c) M. Oki, H. Iwamura, Tetrahedron Lett. (1966) 2917.
26. (d) W.J. Burlant, E.S. Gould, J. Am. Chem. Soc. 76 (1954) 5775.
27. (e) T.W. Cambell, H.G. Walker, G.M. Coppinger, Chem. Rev. 50 (1952) 279.
28. (f) R. Gaithwaite, W.J. Kenyon, H. Phillips, J. Chem. Soc. (1928) 2280.
29. In general, selenurane is more stable when an electron-withdrawing group lies at the apical position.
30. R.S. Berry, J. Chem. Phys. 32 (1960) 933.
31. (a) H. Takada, K. Ohe, S. Uemura, Angew. Chem. Int. Ed. Engl. 38 (1999) 1288.
32. (b) H. Takada, M. Oda, A. Oyamada, K. Ohe, S. Uemura, Chirality 12 (2000) 299.
33. (a) J.F. Bower, C.J. Martin, D.J. Rawson, A.M.Z. Slawin, J.M.J. Williams, J. Chem. Soc. Perkin Trans 1. (1996) 333.
34. (b) J.F. Bower, J.M.J. Williams, Tetrahedron Lett. 35 (1994) 7111.
35. K. Tsujihara, N. Furukawa, K. Oae, S. Oae, Bull. Chem. Soc. Jpn. 42 (1969) 2631.
36. A. Bondi, J. Phys. Chem. 68 (1964) 441.
37. (a) M. Iwaoka, S. Tomoda, Phosphorus Sulfur Silicon Relat. Elements 67 (1992) 125.
38. (b) M. Iwaoka, S. Tomoda, J. Org. Chem. 60 (1995) 5299.
39. (c) M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 118 (1996) 8077.
40. (d) G. Mugesh, H.B. Singh, R.J. Butcher, Tetrahedron: Asymmetry 10 (1999) 237.
41. Some recent examples of stereocontrolled reaction using organoselenium compounds including the Se⋯N or Se⋯O interactions: (a) K. Fujita, K. Murata, M. Iwaoka, S. Tomoda, Tetrahedron 53 (1997) 2029. (b) S. Fukuzawa, K. Takahashi, H. Kato, H. Yamazaki, J. Org. Chem. 62 (1997) 7711. (c) T. Wirth, G. Fragale, M. Spichty, J. Am. Chem. Soc. 120 (1998) 3376 and refs. cited therein.
42. Some recent examples of stereocontrolled reaction using organoselenium compounds including the Se⋯N or Se⋯O interactions: (a) K. Fujita, K. Murata, M. Iwaoka, S. Tomoda, Tetrahedron 53 (1997) 2029. (b) S. Fukuzawa, K. Takahashi, H. Kato, H. Yamazaki, J. Org. Chem. 62 (1997) 7711. (c) T. Wirth, G. Fragale, M. Spichty, J. Am. Chem. Soc. 120 (1998) 3376 and refs. cited therein.
43. Some recent examples of stereocontrolled reaction using organoselenium compounds including the Se⋯N or Se⋯O interactions: (a) K. Fujita, K. Murata, M. Iwaoka, S. Tomoda, Tetrahedron 53 (1997) 2029. (b) S. Fukuzawa, K. Takahashi, H. Kato, H. Yamazaki, J. Org. Chem. 62 (1997) 7711. (c) T. Wirth, G. Fragale, M. Spichty, J. Am. Chem. Soc. 120 (1998) 3376 and refs. cited therein.
44. (a) Y. Nishibayashi, J.D. Singh, K. Segawa, S. Fukuzawa, S. Uemura, J. Chem. Soc. Chem. Commun. (1994) 1375.
45. (b) Y. Nishibayashi, K. Segawa, J.D. Singh, S. Fukuzawa, K. Ohe, S. Uemura, Organometallics 15 (1996) 370.
46. M.J. McKennon, A.I. Meyers, J. Org. Chem. 58 (1993) 3568.
47. Although the reason is not yet clear, combustion analysis of the selenimides 3b, 3c and 3d does not give the expected values even after many attempts.
48. D.P. Schumacker, J.E. Clark, B.L. Murphy, P.A. Fischer, J. Org. Chem. 55 (1990) 5291.
49. C. Bolm, K. Weickhardt, M. Zehnder, T. Ranff, Chem. Ber. 124 (1991) 1173.
50. SMART and SAINT, Area Detector Control and Integration Software, Bruker Analytical X-ray Systems, Madison, WI, 1998.
51. G.M. Sheldrick, SHELXTL, Program for the Solution and Refinement of Crystal Structures, Bruker Analytical X-ray Systems, Madison, WI, 1998.
52. G.M. Sheldrick, SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Göttingen, Germany, 1996.