Optical resolution of selenonium imides stabilized by an 8-dimethylamino-1-naphthyl group

Bulletin of the Chemical Society of Japan

Volumn 80, Issue 12, 2007, Pages 2389-2394

  Soma, Takahiro ^a   Kamigata, Nobumasa ^a   Hirabayashi, Kazunori ^a   Shimizu, Toshio ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATIONS; AMINO GROUPS; CHROMATOGRAPHIC RESOLUTIONS; CIRCULAR DICHROISMS; INTRAMOLECULAR COORDINATIONS; NAPHTHYL GROUPS; OPTICAL RESOLUTIONS; OPTICALLY ACTIVES; SELENIUM ATOMS; SOLID STATES; SPECIFIC ROTATIONS;

COPYING; DICHROISM; OPTICAL PROPERTIES; SELENIUM; SOLID SOLUTIONS;

AMINES;

EID: 58149152546     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.80.2389     Document Type: Article

References (62)

1. For books, see: a) P. Metzner, A. Thuillier, Sulfur Reagents in Organic Synthesis, Academic Press, London, 1993.
2. b) The Chemistry of Sulpkones and Sulphoxides, ed. by S. Patai, A. Rappoport, C. J. M. Stirling, Wiley, New York, 1988.
3. c) The Chemistry of the Sulphonium Group, ed. by C. J. M. Stirling, S. Patai, Wiley, New York, 1981.
4. d) M. Mikołajczyk, J. Drabowicz, Top. Stereochem. 1982, 13, 333.
5. For books, see: a) Organoselenium Chemistry, ed. by T. G. Back, Oxford University Press, New York, 1999.
6. b) The Chemistry of Organic Selenium and Tellurium Compounds, ed. by S. Patai, Z. Rappoport, Wiley, New York, 1987.
7. c) Organoselenium Chemistry, ed. by D. Liotta, Wiley, New York, 1987.
8. d) C. Paulmier, Selenium Reagents and Intermediates in Organic Synthesis, Pergamon, Oxford, 1986.
9. For reviews, see: a) N. Kamigata, T. Shimizu, Rev. Heteroat. Chem. 1991, 4, 226.
10. b) T. Shimizu, N. Kamigata, Org. Prep. Proced. Int. 1997, 29, 603.
11. c) T. Shimizu, N. Kamigata, Rev. Heteroat. Chem. 1998, 18, 11.
12. For reviews, see: a) T. Wirth, Angew. Chem. 2000, 39, 3740.
13. b) T. Wirth, Tetrahedron 1999, 55, 1.
14. c) Y. Nishibayashi, S. Uemura, Rev. Heteroat. Chem. 1996, 14, 83.
15. d) N. Komatsu, S. Uemura, Adv. Detailed React. Mech. 1995, 4, 74.
16. Selenoxide: a) D. N. Jones, D. Mundy, R. D. Whitehouse, J. Chem. Soc. D 1970, 86.
17. b) N. Zylber, J. Zylber, A. Gaudemer, J. Chem. Soc., Chem. Commun. 1978, 1084.
18. c) T. G. Back, N.Ibrahim, D. J. McPhee, J. Org. Chem. 1982, 47, 3283.
19. d) F. A. Davis, J. M. Billmers, O. D. Stringer, Tetrahedron Lett. 1983, 24, 3191.
20. e) F. A. Davis, O. D. Stringer, J. P. McCauley, Jr., Tetrahedron 1985, 41, 4141.
21. f) T. Shimizu, M. Kobayashi, J. Org. Chem. 1987, 52, 3399.
22. g) T. Shimizu, K. Kikuchi, Y. Ishikawa, I. Ikemoto, M. Kobayashi, N. Kamigata, J. Chem. Soc., Perkin Trans. 1 1989, 597.
23. h) F. A. Davis, R. T. Reddy, M. C. Weismiller, J. Am. Chem. Soc. 1989, 111, 5964.
24. i) F. A. Davis, R. T. Reddy, J. Org. Chem. 1992, 57, 2599.
25. j) T. Takahashi, N. Nakano, T. Koizumi, Chem. Lett. 1996, 207.
26. k) T. Shimizu, M. Enomoto, H. Taka, N. Kamigata, J. Org. Chem. 1999, 64, 8242.
27. l) T. Soma, T. Shimizu, K. Hirabayashi, N. Kamigata, Heteroat. Chem. 2007, 18, 301.
28. m) H. Taka, A. Matsumoto, T. Shimizu, N. Kamigata, Chem. Lett. 2000, 726.
29. n) H. Taka, A. Matsumoto, T. Shimizu, N. Kamigata, Heteroat. Chem. 2001, 12, 227.
30. Selenonium ylide: a) K. Sakaki, S. Oae, Tetrahedron Lett. 1976, 17, 3703.
31. b) N. Kamigata, Y. Nakamura, K. Kikuchi, I. Ikemoto, T. Shimizu, H. Matsuyama, J. Chem. Soc, Perkin Trans. 1 1992, 1721.
32. c) T. Takahashi, N. Kurose, S. Kawanami, A. Nojiri, Y. Arai, T. Koizumi, M. Shiro, Chem. Lett. 1995, 379.
33. Selenonium salt: a) W. J. Pope, A. Neville, J. Chem. Soc., Trans. 1902, 81, 1552.
34. b) F. G. Holliman, F. G. Mann, J. Chem. Soc. 1945, 37.
35. c) M. Kobayashi, K. Koyabu, T. Shimizu, K. Umemura, H. Matsuyama, Chem. Lett. 1986, 2117.
36. Seleninic acid: a) T. Shimizu, I. Watanabe, N. Kamigata, Angew. Chem., Int. Ed. 2001, 40, 2460.
37. b) Y. Nakashima, T. Shimizu, K. Hirabayashi, N. Kamigata, M. Yasuib, M. Nakazatob, F. Iwasaki, Tetrahedron Lett. 2004, 45, 2301.
38. c) Y. Nakashima, T. Shimizu, K. Hirabayashi, M. Yasui, M. Nakasato, F. Iwasaki, N. Kamigata, Bull. Chem. Soc. Jpn. 2005, 78, 710.
39. Seleninamide: Y. Nakashima, T. Shimizu, K. Hirabayashi, N. Kamigata, J. Org. Chem. 2005, 70, 868.
40. Seleninate ester: Y. Nakashima, T. Shimizu, K. Hirabayashi, F. Iwasaki, M. Yamasaki, N. Kamigata, J. Org. Chem. 2005, 70, 5020.
41. Telluroxide: a) T. Shimizu, Y. Yamazaki, H. Taka, N. Kamigata, J. Am. Chem. Soc. 1997, 119, 5966.
42. b) H. Taka, Y. Yamazaki, T. Shimizu, N. Kamigata, J. Org. Chem. 2000, 65, 2127.
43. Telluronium ylide: N. Kamigata, A. Matsuhisa, H. Taka, T. Shimizu, J. Chem. Soc, Perkin Trans. 1 1995, 821.
44. Telluronium salt: a) T. M. Lowry, F. L. Gilbert, J. Chem. Soc. 1929, 2867.
45. b)F. G. Holliman, F. G. Mann, J. Chem. Soc. 1945, 37.
46. c) T. Shimizu, T. Urakubo, P. Jin, M. Kondo, S. Kitagawa, N. Kamigata, J. Organomet. Chem. 1997, 539, 171.
47. d) J. Zhang, S. Saito, T. Koizumi, J. Org. Chem. 1998, 63, 5423.
48. Tellurinic acid: a) Y. Nakashima, T. Shimizu, K. Hirabayashi, N. Kamigata, Org. Lett. 2004, 6, 2575.
49. b) Y. Nakashima, T. Shimizu, K. Hirabayashi, M. Yasui, M. Nakasato, F. Iwasaki, N. Kamigata, Tetrahedron: Asymmetry 2004, 15, 3791.
50. Telluronium imide: a) T. Shimizu, Y. Machida, N. Kamigata, Eur. J. Org. Chem. 2002, 2265.
51. b) T. Shimizu, Y. Machida, N. Kamigata, Heteroat. Chem. 2003, 14, 523.
52. V. P. Krasnov, V. I. Naddaka, V. I. Minkin, Zh. Org. Khim. 1981, 17, 445.
53. N. Kamigata, H. Taka, A. Matsuhisa, H. Matsuyama, T. Shimizu, J. Chem. Soc., Perkin Trans. 1 1994, 2257.
54. a) H. Taka, T. Shimizu, F. Iwasaki, M. Yasui, N. Kamigata, J. Org. Chem. 1999, 64, 7433.
55. b) T. Shimizu, N. Seki, H. Taka, N. Kamigata, J. Org. Chem. 1996, 61, 6013.
56. a) Y. Nishibayashi, T. Chiba, K. Ohe, S. Uemura, J. Chem. Soc., Chem. Commun. 1995, 1243.
57. b) N. Kurose, T. Takahashi, T. Koizumi, J. Org. Chem. 1996, 61, 2932.
58. c) H. Takada, Y. Miyake, K. Ohe, S. Uemura, Chem. Commun. 1998, 1557.
59. d) Y. Miyake, M. Oda, A. Oyamada, H. Takada, K. Ohe, S. Uemura, J. Organo met. Chem. 2000, 611, 475.
60. a) S. Hayashi, H. Wada, T. Ueno, W. Nakanishi, J. Org. Chem. 2006, 71, 5574.
61. b) W. Nakanishi, S. Hayashi, A. Sakaue, G. Ono, Y. Kawada, J. Am. Chem. Soc. 1998, 120, 3635.
62. S. Tamagaki, S. Oae, K. Sakaki, Tetrahedron Lett. 1975, 16, 649.