Catalytic asymmetric coupling of 2-naphthols by chiral tridentate oxovanadium(IV) complexes

Organic Letters

Volumn 3, Issue 6, 2001, Pages 869-872

  Hon, Sang Wen ^a   Li, Chun Hsin ^a   Kuo, Jen Huang ^a   Barhate, N B ^a   Liu, Yi Hung ^b   Wang, Yu ^b   Chen, Chien Tien ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000441860     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015505o     Document Type: Article

References (49)

1. For recent reviews, see: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
2. (b) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
3. (c) Pu, L. Chem. Rev. 1998, 98, 2405.
4. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley and Sons: New York, 1994.
5. For leading references, see: (e) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979.
6. (f) Ishihara, K.; Nakamura, H.; Yamamoto, H. J. Am. Chem. Soc. 1999, 121, 7720.
7. (a) Noyori, R. Chem. Soc. Rev. 1989, 18, 187.
8. (b) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
9. (a) Feringa, B.; Wynberg, H. Bioorg. Chem. 1978, 7, 397.
10. (b) Kawashima, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993, 66, 2002.
11. Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
12. Miyano, S.; Kawahara, K.; Inoue, Y.; Hashimoto, H. Tetrahedron Lett. 1987, 355.
13. Pirkle, W. H.; Schreiner, J. L. J. Org. Chem. 1981, 46, 4988.
14. (a) Smrčina, M.; Lorenc, M.; Hanuš, V.; Sedmera, P.; Kočovský, P. J. Org. Chem. 1992, 57, 1917.
15. (b) Srmrčina, M.; Poláková, J.; Vyskočil, S.; Kočovský, P. J. Org. Chem. 1993, 58, 4534.
16. (c) Smrčina, M.; Vyskočil, S.; Mača, B.; Polášek, M.; Claxton, T. A.; Abbott, A. P.; Kočovský, P. J. Org. Chem. 1994, 59, 2156.
17. (d) Brussee, J.; Groenendijk, J. L. G.; te Kopple, J. M.; Jansen, A. C. A. Tetrahedron 1985, 16, 3313.
18. Osa, T.; Kashiwagi, Y.; Yanagisawa, Y.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1994, 2535.
19. (a) Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. J. Chem. Soc., Chem. Commun. 1993, 909.
20. 9c
21. (c) Irie, R.; Masutani, K.; Katsuki, T. Synlett 2000, 1433.
22. (a) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264 and references therein.
23. 2-sparteine-AgCl based system was first demonstrated by Smrčina and Kočovský (ref 7b).
24. (a) Nakajima, K.; Kojimo, M.; Fujita, J. Chem. Lett. 1986, 1483.
25. (b) Takai, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1990, 1657.
26. (c) Bolm, C.; Bienewald, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2640.
27. (a) Dichmann, K.; Hamer, G.; Nyburg, S. C.; Reynold, S. W. F. J. Chem. Soc. D 1970, 1295.
28. (b) For DMSO complexes, see: Agarwal, K.; Singh, G. J. Indian Chem. Soc. 1986, 63, 926.
29. Chen, C.-T.; Hon, S.-W.; Weng, S.-S. Synlett 1999, 816.
30. Hwang, D. R.; Chen, C. P.; Uang, B. J. J. Chem. Soc., Chem. Commun. 1999, 1207.
31. (a) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686 and references therein.
32. (b) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500.
33. (a) Kiyooka, S.-I.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276.
34. (b) Parmee, E. R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365.
35. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
36. (a) Annis, D. A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 4147.
37. (b) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296.
38. Theriot, L. J.; Carlisle, G. O.; Hu, H. J. J. Inorg. Nul. Chem. 1969, 31, 2841.
39. See the Supporting Information.
40. Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011.
41. 4.
42. Defined as (%R - %S/%R + %S) x 100.
43. In almost all instances, the crystals crashed out in racemic form. Nevertheless, the solids collected after concentration of the mother liquors turned out to be enantiomerically pure.
44. A preformed hydrogen-bonded 1:1 complex was used as the coupling substrate, see: Ding, K.; Xu, Q.; Wang, Y.; Liu, J.; Yu, Z.; Du, B.; Wu, Y.; Koshima, H.; Matsuura, T. J. Chem. Soc., Chem. Commun. 1997, 693.
45. (a) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
46. (b) Zhou, X. G.; Yu, X. Q.; Huang, J. S.; Li, S. G.; Li, L. S.; Che, C. M. J. Chem. Soc., Chem. Commun. 1999, 1789.
47. (c) Vyskočil, S.; Jaracz, S.; Smrčina, M.; Stícha, M.; Hanuš, V.; Polášek, M.; Kočovský, P. J. Org. Chem. 1998, 63, 7727.
48. V complex from salicylaldehyde and L-alanine, see: Nakajima, K.; Kojima, M.; Toriumi, K.; Saito, K.; Fujita, J. Bull. Chem. Soc. Jpn. 1989, 62, 760.
49. (b) See also: Nitta, H.; Yu, D.; Kudo, M.; Mori, A.; Inoue, S. J. Am. Chem. Soc. 1992, 114, 7969.