A Facile Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyl and 2,2′-Diamino-1,1′-binaphthyl by Oxidative Coupling Using Copper(II) Chloride

Synlett

Volumn 1991, Issue 4, 1991, Pages 231-232

  Smrčina, Martin ^a   Lorenc, Miroslav ^b   Hanuš, Vladimír ^a   Kočovský, Pavel ^c  

^a J Heyrovský Institute of Physical Chemistry and Electrochemistry ČSAV ^*  (Slovakia)

^b Research Institute for Antibiotics and Biotransformations ^*  (Slovakia)

^c UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85064428639     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1991-20688     Document Type: Article

References (55)

1. Brown, K. J.; Murdoch, I. R. J. Am. Chem. Soc. 1984,106, 7843.
2. (a) Noyori, R.; Tomino, L; Tanimoto, Y. J. Am. Chem. Soc. 1979,101,3129.
3. (b) Noyori, R.; Tomino, L; Nishizawa, M. J. Am. Chem. Soc. 1979, 101, 5844.
4. (c) Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984,106,6709.
5. (d) Noywi, R.; Tomino, L; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984,106,6717.
6. (e) Shizawa, M.; Yamada, M.; Noyori, R. Tetrahedron Lett, 1984, 22,247.
7. (a) Sogah, G. D. Y.; Cram, D. J. J. Am. Chem. Soc. 1975, 97, 1259.
8. (b) Sogah, G. D. U.; Cram, D. J. J. Am. Chem. Soc. 1976, 98, 3038.
9. (c) Sousa, L. R.; Sogah, G. D. Y.; Hoffman, D. H.; Cram, D. J. J. Am. Chem. Soc. 1978,100, 4569.
10. (d) Timko, J. M.; Helgeson, R C; Cram, D. J. J. Am. Chem. Soc. 1978,100,2828.
11. (c) Sogah, G. D. Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035.
12. (f) Cram, D. J.; Cram, J. M. Acc. Chan. Res. 1978,11, 8.
13. (g) Kyba, E. P.; Gokcl, G. W.; de Jong, R; Koga, K.; Sousa, K.; Sousa, L. R.; Siegel, M. C; Kolan, L.; Sogah, G. D. Y.; Cram, D. J. J. Org. Chem. 1977, 42, 4173.
14. (h) Ctam, D. J. US pat. 4,043, 979 (1977), Chem. Abstr. 1978, 89, 109618.
15. Mikes, P.; Boshart, G. J. Chem. Soc., Chem. Common. 1978,173.
16. (a) Scebach, D.; Beck, A. K.; Rogo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673.
17. (b) Ollvero, A. G.; Weidmann, B.; Scebach, D. Helv. Chem. Acta. 1981, 64, 2485.
18. (c) Ji-Tao, W.; Xinju, P.; Ji-Min, Q. Synthesis 1989, 291.
19. (a) Miyano, S.; Honda, S.; Shimizu, K.; Tagami, K.; Hashimoto, H. Btdl. Chem. Soc. Jpn. 1984,57, 1943.
20. (b) Miyano, S.; Tobita, M.; Nawa, M. Sato, S.; Hashimoto, H. J. Chem. Soc., Chem. Common. 1980, 1233.
21. (c) Miyano, S.; Tobita, M.; Hadiimoto, H. Bull. Chem. Soc. Jpn. 1981, 54,3522.
22. (a) Toda, P.; Tanaka, P.; Nagamatsu, S. Tetrahedron Lett. 1984, 25, 4929.
23. (b) Toda, P.; Mori, K. J. Chem. Soc. Chem. Commun. 1986, 1357.
24. (a) Gatnier-Saillerot, A.; Albertini, J. P.; Collet, A.; Paury, L.; Pastor, J.-M.; Tosi, L. J. Chem. Soc. Dalton Trans. 1981, 2544.
25. (b) Bey, P.; Vevert, J.-P.; von Dorselauer, V.; Kolb, M. J. Org. Chem. 1979, 44, 2732.
26. (c) Jacques, J.; Pouquey, C; Viterbo, R. Tetrahedron Lett. 1971, 4617.
27. (d) Viterbo, R.; Jacques, J. German Offen. 2,212,660 (1972);
28. Chem. Abstr. 1973, 78, 43129.
29. (e) Arnold, W.; Daly, J. J.; Imhof, R.; Kyburz, E. Tetrahedron Lett. 1983,24, 343.
30. (f) Imhof, R.; Kybura, E., Daly, J. J. J. Med. Chem. 1984,27, 165.
31. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noywi, R J. Am. Chem. Soc. 1980, 702,7932.
32. (b) Brown, K. J.; Berry, M. S.; Watermann, K C; Lingenfeltcr, D.; Murdoch, J. R. J. Am. Chem. Soc. 1984, 106,4717.
33. (c) Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R Tetrahedron Lett. 1984, 40, 1245.
34. (d) Takaya, H.; Mashima, K.; Koyono, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akugatawa, S.; Noyori, R J. Org. Chem. 1986, 51, 629.
35. (e) Tani, K.; Yamagata, T.; Akugatawa, T.; Kumobayashi, H.; Taketomi, T.; Takaya, R; Miyashita, A.; Noywi, R; Otsuka, S. Am. Chem. Soc. 1984,106, 5208.
36. (a) Miyano, S.; Nawa, M.; Mori, A.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2171.
37. (b) Grobbs, R H.; deVries, R A. Tetrahedron Lett. 1977, 1879.
38. (c) Miyano, S.; Nawa, M.; Hashimoto, H. Chem Lett. 1980, 729.
39. (d) Tamao, K.; Yamamoto, H.; Matsumoto, H.; Miyake, N.; Hayashi, T.; Kumada, M. Tetrahedron Lett. 1977, 1389.
40. Kabuto, K.; Yoshida, T.; Yamaguchi, S.; Miyano, S.; Haslimoto, R J. Org. Chem. 1985, 50, 3013.
41. (a) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585.
42. (b) Mazaleyrat, J.-P. Tetrahedron Lett. 1983, 24, 1243.
43. Hovorka, M.; Gflnterovd, J.; Zdvada, J. Tetrahedron Lett. 1990,57,413.
44. (a) Meisenheimer, J.; Witte, K. Chem. Ber. 1903,36,4158.
45. (b) Hantzsch, A.; Schmiedel, M. Chem. Ber. 1897,30, 82.
46. (c) Clemo, O, R.; Dawson, E. C. J. Chem. Soc. 1939,1114.
47. (d) Erode, W. R.; Brooks, R. E. J. Am. Chem. Soc. 1941, 63,923.
48. (e) Krolik, L. G.; Llkashevich, V. O. Dokl. Akad. Nauk SSSR 1949,65, 37;
49. Chem. Abstr. 1949,43, 5774.
50. (f) Mislow, K.; Grasemann, P. A. J. Org. Chem. 1958, 23, 2027.
51. (g) Murdoch, K. J.; Beny, M. S.; Murdoch, J. R. J. Org. Chem. 1985,50,4345.
52. (h) Sannicolo, F. Tetrahedron Lett. 1985, 26, 119.
53. (i) Shine, R J.; Gruszecka, E.; Subotkowski, W.; Brownawell, M.; Fillipo, J. S. J. Am. Chem. Soc. 1985,707,3218.
54. Feringa, B.; Wynberg, H. Bioorg. Chem. 1978,7,397.
55. Brusse, J.; Groenendijk, J. L. G.; te Koppele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313.