Stereospecific cycloadditions of cis- and trans-N-benzyl-1,2-diphenylaziridines with C60

Heterocyclic Communications

Volumn 2, Issue 6, 1996, Pages 545-548

  Matsumoto, Kiyoshi ^a   Ciobanu, Mona ^a   Katsura, Hideki ^a   Ohta, Ryuji ^a   Uchida, Takane ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF FUKUI   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000363395     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (76)

1. For recent reviews, see: (a) H. W. Kroto, A. W. Allaf, S. P. Balm, Chem. Rev. 91; 1213 (1992) (b) Special issue on fullerenes, Acc. Chem. Res. 25, 98 (1992) (c) Special issue on fullerenes, Carbon 30, 1135 (1992) (d) R. Taylor, D. R. M. Walton, Nature 363, 685 (1993) (e) A. Hirsch, Angew. Chem. Int. Ed. Engl. 32, 1138 (1993) (f) A. Hirsch,Synthesis895 (1995) (g) S. Eguchi, M. Ohno, S. Kojima, N. Koide, A. Yashiro, Y. Shirakawa, H. Ishida,FullereneSci. Tech. 4,303 (1996) (h) Special issue on fullerenes, Tetrahedron 52, 4925 (1996).
2. For recent reviews, see: (a) H. W. Kroto, A. W. Allaf, S. P. Balm, Chem. Rev. 91; 1213 (1992) (b) Special issue on fullerenes, Acc. Chem. Res. 25, 98 (1992) (c) Special issue on fullerenes, Carbon 30, 1135 (1992) (d) R. Taylor, D. R. M. Walton, Nature 363, 685 (1993) (e) A. Hirsch, Angew. Chem. Int. Ed. Engl. 32, 1138 (1993) (f) A. Hirsch,Synthesis895 (1995) (g) S. Eguchi, M. Ohno, S. Kojima, N. Koide, A. Yashiro, Y. Shirakawa, H. Ishida,FullereneSci. Tech. 4,303 (1996) (h) Special issue on fullerenes, Tetrahedron 52, 4925 (1996).
3. For recent reviews, see: (a) H. W. Kroto, A. W. Allaf, S. P. Balm, Chem. Rev. 91; 1213 (1992) (b) Special issue on fullerenes, Acc. Chem. Res. 25, 98 (1992) (c) Special issue on fullerenes, Carbon 30, 1135 (1992) (d) R. Taylor, D. R. M. Walton, Nature 363, 685 (1993) (e) A. Hirsch, Angew. Chem. Int. Ed. Engl. 32, 1138 (1993) (f) A. Hirsch,Synthesis895 (1995) (g) S. Eguchi, M. Ohno, S. Kojima, N. Koide, A. Yashiro, Y. Shirakawa, H. Ishida,FullereneSci. Tech. 4,303 (1996) (h) Special issue on fullerenes, Tetrahedron 52, 4925 (1996).
4. For recent reviews, see: (a) H. W. Kroto, A. W. Allaf, S. P. Balm, Chem. Rev. 91; 1213 (1992) (b) Special issue on fullerenes, Acc. Chem. Res. 25, 98 (1992) (c) Special issue on fullerenes, Carbon 30, 1135 (1992) (d) R. Taylor, D. R. M. Walton, Nature 363, 685 (1993) (e) A. Hirsch, Angew. Chem. Int. Ed. Engl. 32, 1138 (1993) (f) A. Hirsch,Synthesis895 (1995) (g) S. Eguchi, M. Ohno, S. Kojima, N. Koide, A. Yashiro, Y. Shirakawa, H. Ishida,FullereneSci. Tech. 4,303 (1996) (h) Special issue on fullerenes, Tetrahedron 52, 4925 (1996).
5. For recent reviews, see: (a) H. W. Kroto, A. W. Allaf, S. P. Balm, Chem. Rev. 91; 1213 (1992) (b) Special issue on fullerenes, Acc. Chem. Res. 25, 98 (1992) (c) Special issue on fullerenes, Carbon 30, 1135 (1992) (d) R. Taylor, D. R. M. Walton, Nature 363, 685 (1993) (e) A. Hirsch, Angew. Chem. Int. Ed. Engl. 32, 1138 (1993) (f) A. Hirsch,Synthesis895 (1995) (g) S. Eguchi, M. Ohno, S. Kojima, N. Koide, A. Yashiro, Y. Shirakawa, H. Ishida,FullereneSci. Tech. 4,303 (1996) (h) Special issue on fullerenes, Tetrahedron 52, 4925 (1996).
6. For recent reviews, see: (a) H. W. Kroto, A. W. Allaf, S. P. Balm, Chem. Rev. 91; 1213 (1992) (b) Special issue on fullerenes, Acc. Chem. Res. 25, 98 (1992) (c) Special issue on fullerenes, Carbon 30, 1135 (1992) (d) R. Taylor, D. R. M. Walton, Nature 363, 685 (1993) (e) A. Hirsch, Angew. Chem. Int. Ed. Engl. 32, 1138 (1993) (f) A. Hirsch,Synthesis895 (1995) (g) S. Eguchi, M. Ohno, S. Kojima, N. Koide, A. Yashiro, Y. Shirakawa, H. Ishida,FullereneSci. Tech. 4,303 (1996) (h) Special issue on fullerenes, Tetrahedron 52, 4925 (1996).
7. For recent reviews, see: (a) H. W. Kroto, A. W. Allaf, S. P. Balm, Chem. Rev. 91; 1213 (1992) (b) Special issue on fullerenes, Acc. Chem. Res. 25, 98 (1992) (c) Special issue on fullerenes, Carbon 30, 1135 (1992) (d) R. Taylor, D. R. M. Walton, Nature 363, 685 (1993) (e) A. Hirsch, Angew. Chem. Int. Ed. Engl. 32, 1138 (1993) (f) A. Hirsch,Synthesis895 (1995) (g) S. Eguchi, M. Ohno, S. Kojima, N. Koide, A. Yashiro, Y. Shirakawa, H. Ishida,FullereneSci. Tech. 4,303 (1996) (h) Special issue on fullerenes, Tetrahedron 52, 4925 (1996).
8. For recent reviews, see: (a) H. W. Kroto, A. W. Allaf, S. P. Balm, Chem. Rev. 91; 1213 (1992) (b) Special issue on fullerenes, Acc. Chem. Res. 25, 98 (1992) (c) Special issue on fullerenes, Carbon 30, 1135 (1992) (d) R. Taylor, D. R. M. Walton, Nature 363, 685 (1993) (e) A. Hirsch, Angew. Chem. Int. Ed. Engl. 32, 1138 (1993) (f) A. Hirsch,Synthesis895 (1995) (g) S. Eguchi, M. Ohno, S. Kojima, N. Koide, A. Yashiro, Y. Shirakawa, H. Ishida,FullereneSci. Tech. 4,303 (1996) (h) Special issue on fullerenes, Tetrahedron 52, 4925 (1996).
9. (a) B. Kräutler, M. Puchberger, Helv. Chim. Acta 76, 1626 (1993)
10. (b) M. F. Meidine, R. Roers, G. J. Langely, A. G. Advent, A. D. Darwish, S. Firth, H. W. Kroto, R. Taylor, D. R. M. Walton, J. Chem. Soc. Chem. Commun. 1342 1993)
11. (c) Y. Rubin, S. I. Khan, D. I. Freedberg, C. Yeretzian, J. Am. Chem. Soc. 115, 344 (1993)
12. (d) S. I. Khan, A. M. Oliver, M. N. Paddon-Row, Y. Rubin, J. Am. Chem. Soc. 115, 4919 (1993)
13. (e) Y.-Z. An. J. L. Anderson. Y. Rubin, J. Org. Chem. 58, 4799 (1993)
14. (f) P. Belik, A. Gūgel, J. Spickermann, K. Müllen, Angew. Chem. Int. Ed. Engl. 32, 78 (1993)
15. (g) S. R. Wilson, Q. Lu, Tetrahedron Lett. 34, 8043 (1993)
16. (h) W. Bidell, R. E. Douthwaite, M. L H. Green, A. H. Stephens, J. F. C. Turner, J. Chem. Soc. Chem. Commun. 1641 (1994)
17. (i) X. Zhang, C. S. Foote, J. Org. Chem. 59, 5235 (1994)
18. (j) A. Gügel, A. Krauss, J. Spickermann, P. Belik, K. Müllen. Angew. Chem. Int. Ed. Engl. 33, 559 (1994)
19. (k) T. G. Linssen, K. Dṻrr, M. Hanack, A. Hirsch, J. Chem. Soc. Chem. Commun. 103 (1995)
20. (I) M. Ohno, S. Kojima, S. Eguchi, J. Chem. Soc. Chem. Commun. 565 (1995)
21. (m) M. Ohno, N. Koide, S. Eguchi, Heterocycl. Commun. 1, 125 (1995)
22. (n) M. Ohno, T. Azuma, S. Kojima, Y. Shirakawa, S. Eguchi, Tetrahedron 52, 4983 (1996)
23. (o) B. Kräutler, J. Maynollo, Tetrahedron 52, 5033 (1996)
24. (p) T.-G. Gregorio, M. Jochen, Tetrahedron 52, 5421 (1996).
25. (a) S. R. Wilson, Y. Wu, N. Kapridis, D. I. Schuster, J. Org. Chem. 58, 6548 (1993)
26. (b) S. R. Wilson, N. Kapridis, Y. Wu, D. I. Schuster, J. Am. Chem. Soc. 115, 8495 (1993)
27. (c) X. Zhang, A. Romero, C. S. Foote, J. Am. Chem. Soc. 115, 11024 (1993)
28. (d) A. M. Rao, P. Zhou, K.-A. Wang, G. T. Hager, J. M. Holden, Y. Wang, W.-T. Lee, X.-X. Bi, P. C. Eklund, D. S. Cornett, M. A. Duncan, I. J. Amster, Science 259, 955 (1993)
29. (e) S. Yamago, A. Takeichi, E. Nakamura, J. Am. Chem. Soc. 116, 1123 (1994)
30. (f) X. Zhang, C. S. Foote, J. Am. Chem. Soc. 117, 4271 (1995)
31. (g) D. I. Schuster, J. Cao, N. Kapridis, Y. Wu, A. W. Jensen, Q. Li, H. Wang, S. R. Wilson, J. Am. Chem. Soc. 118, 5639 (1996).
32. E. Beer, M. Feuerer, A. Knorr, A. Mirlach, J. Daub, Angew. Chem. Int. Ed. Engl. 33, 1087 (1994).
33. (a) T. Suzuki, Q. Li, K. C. Khemani, F. Wudl, Ö. Almarsson, Science 254, 1186 (1991)
34. (b) F. Wudl, Acc. Chem. Res. 25, 157 (1992)
35. (c) T. Suzuki, Q. Li, K. C. Khemani, F. Wudl, Ö. Almarsson, J. Am. Chem. Soc. 114, 7300 (1992)
36. (d) S. Shi, K. C. Khemani, Q. Li, F. Wudl, J. Am. Chem. Soc. 10656 (1992)
37. (e) T. Suzuki, Q. Li, K. C. Khemani, F. Wudl, J. Am. Chem. Soc. 7301 (1992)
38. (f) R. Sijbesma, G. Srdanov, F. Wudl, J. A. Castoro, C. Wilkins, S. H. Friedman, D. L. DeCamp, G.L Kenyon, J. Am. Chem. Soc. 115, 6510 (1993)
39. (g) A. B. Smith III, R. M. Strongin, L. Brard, G. T. Furst, W. J. Romanow, K. G. Owens, R. C. King, J. Am. Chem. Soc. 115, 5829 (1993)
40. (h) H. L. Anderson, R. Faust, Y. Rubin, F. Dieterich, Angew. Chem. Int. Ed. Engl. 33, 1366 (1994).
41. (a) S. R. Wilson, Y. Wu, J. Chem. Soc. Chem. Commun. 784 (1993)
42. (b) M. Prato, Q. C. Li, F. Wudl, V. Lucchini, J. Am. Chem. Soc. 115, 1148 (1993)
43. (c) C. J. Hawker, K. L. Wooley, J. M. Fréchet, J. Chem. Soc. Chem. Commun. 925 (1994)
44. (d) C. J. Hawker, P. M. Saville, J. W. White, J. Org. Chem. 59, 3503 (1994)
45. (e) M. Yan, S. X. Cai, J. F. W. Keana, J. Org. Chem. 59, 5951 (1994)
46. (f) M. R. Banks, J. I. G. Cadogan, I. Gosney. P. K. G. Hodgson. P. R. R. Langridge-Smith, D. W. H. Rankin, J. Chem. Soc. Chem. Commun. 1365 (1994)
47. (g) M. R. Banks, I. Gosney, P. K. G. Hodgson, P. R. R. Langridge-Smith, J. R. A. Millar, A. T. Taylor, J. Chem. Soc. Chem. Commun. 885 (1995)
48. (h) T. Ishida, K. Tanaka, T. Nogami, Chem. Lett. 561 (1994)
49. (i) J. Averdung, H. Luftmann, J. Mattay, K.-U. Claus, W. Abraham, Tetrahedron Lett. 36, 2957 (1995).
50. D. Brizzolara, J. T. Ahlemann, H. W. Roetsky, K. Keller, Bull. Soc. Chim. Fr. 130, 745 (1993).
51. (a) J. Averdung, E. Albrech, J. Lauterwein, H. Luftmann, J. Mattay, H. Mohn, W. H. Müller, H.-Ulrich Meer, Chem. Ber. 127, 787 (1994)
52. (b) J. Averdung, J. Mattay, Tetrahedron 52, 5407 (1996).
53. (a) T. Akasaka, W. Ando, K. Kobayashi, S. Nagase, J. Am. Chem. Soc. 115, 10366 (1993)
54. (b) T. Akasaka, E. Mitsuhida, W. Ando, K. Kobayashi, S. Nagase, J. Chem. Soc. Chem. Commun. 1529 (1995).
55. (a) M. S. Meier, M. Poplawska, J. Org. Chem. 58, 4524 (1993)
56. (b) M. S. Meier, M. Poplawska, A. L Compton, J. Shaw, J. P. Selegue, T. F. Guarr, J. Am. Chem. Soc. 116, 7044 (1994)
57. (c) H. Imgartinger, C.-M. Köhler, U. Huber-Patz, W. Krätschmer, Chem. Ber. 127, 437 (1994)
58. (d) M. S. Meier, Tetrahedron 52, 5043 (1996).
59. (a) X. Zhang, M. Willems, C. S. Foote, Tetrahedron Lett. 34, 8187 (1993)
60. (b) M. Maggini ,G. Scorrano, J. Am. Chem. Soc. 115, 9798 (1993)
61. (c) M. Maggini, G. Scorrano, A. Bianco, C. Toniolo, R. P. Sijbesma, F. Wudl, M. Prato, J. Chem. Soc. Chem. Commun. 305 (1994)
62. (d) M. Maggini, A. Karlsson, L Pasimeni, G. Scorrao, M. Prato, L Valli, Tetrahedron Lett. 35, 2985 (1994)
63. (e) L-H. Shu, G.-W. Wang, S.-H. Wu, Tetrahedron Lett. 36, 3871 (1995)
64. (f) M. Iyoda, F. Sutana, M. Komatsu, Chem. Lett. 1133 (1995)
65. (g) S. R. Wilson, Y. Wang, J. Cao, X. Tan, Tetrahedron Lett. 37, 775 (1996).
66. (a) J. W. Lown, Azomethine Ylides, in A. Padwa (Ed.), 1,3-Dipolar Cycloadditions Chemistry, John Wiley and Sons, New York, 1984, vol 1, pp 653
67. (b) O. Tsuge, S. Kanemasa, Adv. Heterocycl. Chem. 45, 231 (1989).
68. For recent references, see: (a) K. Matsumoto, Y. Ikemi, C. Takayama, K. Aoyama, T. Uchida, Chem. Lett. 1647 (1990) (b) K. Matsumoto, H. Iida, T. Uchida, Y. Yabe, A. Kakehi, Chem. Express 8, 609 (1993) (c) K. Matsumoto, H. Iida, T. Uchida, Y. Yabe, A. Kakehi, J. W. Lown, Can. J. Chem. 72, 2108 (1994) (d) R. Huisgen, K. Matsumoto, C. H. Ross, Heterocycles 15, 1131 (1981).
69. For recent references, see: (a) K. Matsumoto, Y. Ikemi, C. Takayama, K. Aoyama, T. Uchida, Chem. Lett. 1647 (1990) (b) K. Matsumoto, H. Iida, T. Uchida, Y. Yabe, A. Kakehi, Chem. Express 8, 609 (1993) (c) K. Matsumoto, H. Iida, T. Uchida, Y. Yabe, A. Kakehi, J. W. Lown, Can. J. Chem. 72, 2108 (1994) (d) R. Huisgen, K. Matsumoto, C. H. Ross, Heterocycles 15, 1131 (1981).
70. For recent references, see: (a) K. Matsumoto, Y. Ikemi, C. Takayama, K. Aoyama, T. Uchida, Chem. Lett. 1647 (1990) (b) K. Matsumoto, H. Iida, T. Uchida, Y. Yabe, A. Kakehi, Chem. Express 8, 609 (1993) (c) K. Matsumoto, H. Iida, T. Uchida, Y. Yabe, A. Kakehi, J. W. Lown, Can. J. Chem. 72, 2108 (1994) (d) R. Huisgen, K. Matsumoto, C. H. Ross, Heterocycles 15, 1131 (1981).
71. For recent references, see: (a) K. Matsumoto, Y. Ikemi, C. Takayama, K. Aoyama, T. Uchida, Chem. Lett. 1647 (1990) (b) K. Matsumoto, H. Iida, T. Uchida, Y. Yabe, A. Kakehi, Chem. Express 8, 609 (1993) (c) K. Matsumoto, H. Iida, T. Uchida, Y. Yabe, A. Kakehi, J. W. Lown, Can. J. Chem. 72, 2108 (1994) (d) R. Huisgen, K. Matsumoto, C. H. Ross, Heterocycles 15, 1131 (1981).
72. 60 conversion.
73. 3), 76.14 (N-CH), 127.74, 128.09, 128.15, 128.37, 128.41, 129.19, 129.41, 130.19, 130.65, 130.81, 131.90, 135.55, 136.41, 136.47, 139.11, 139.64, 141.27, 141.64, 141.74, 141.79, 141.90, 141.92, 142.29, 142.39, 144.13, 144.42, 144.87, 145.00, 145.03, 145.27. 145.63. 145.70, 145.86, 145.96, 146.06, 146.49, 147.07, 153.28, 154.00.
74. R. B. Woodward, R. Hoffmann. Angew. Chem, Int. Ed. Engl. 8, 781 (1969).
75. 2 = 1/1) & 67.53 (C-3a), 76.32 (C-3), 76.37 (C-2), 79.85 (C-1), 111.56 (C-9), 121.05 (C-7), 127.71, 127.82, 128.32, 128.43, 129.22, 129.78, 129.90, 131.03, 133.33, 133.98, 135.36, 135.66, 136.19, 136.87, 137.23, 137.66, 138.61, 139.22, 139.73, 140.10, 141.38, 141.47, 141.63, 141.68, 141.77, 141.84, 141.92, 141.95, 141.98, 142.03, 142.07, 142.35, 142.39. 142.48, 142.54, 142.57, 142.71, 142.90, 142.98, 143.64, 144.02, 144.07, 144.25, 144.68, 144.84, 144.96, 145.05, 145.12, 145.14, 145.17, 145.35, 145.68, 145.78, 145.82, 145.91, 145.96, 146.00, 146.09, 146.24, 146.69, 146.83, 147.81, 151.32, 152.40, 155.71, 157.13.
76. X. Shi, W. B. Caldwell, K. Chen, C. A. Mirkin, J. Am. Chem. Soc. 116, 11598 (1994).