Novel achiral biphenol-derived diastereomeric oxovanadium(IV) complexes for highly enantioselective oxidative coupling of 2-naphthols

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4532-4535

  Lou, Z ^a   Liu, Q ^a   Gong, L ^a   Cui, X ^a   Mi, A ^a   Jiang, Y ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric catalysis; Binaphthols; C C coupling; N,O ligands; Vanadium

Indexed keywords

CATALYSTS; COMPLEXATION; OXIDATION; PHENOLS;

ENANTIOSELECTIVES;

STEREOCHEMISTRY;

2 NAPHTHOL; OXOVANADIUM; UNCLASSIFIED DRUG; VANADIUM DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; CONFORMATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; OXIDATION;

EID: 0037011404     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4532::AID-ANIE4532>3.0.CO;2-5     Document Type: Article

References (42)

1. a) R. Noyori, Asymmetric Catalysis in the Organic Synthesis; Wiley, New York, 1994;
2. b) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345;
3. c) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen. A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
4. d) K. A. Jørgensen, Angew. Chem. 2000, 112, 3702; Angew. Chem. Int. Ed. 2000, 39, 3558;
5. d) K. A. Jørgensen, Angew. Chem. 2000, 112, 3702; Angew. Chem. Int. Ed. 2000, 39, 3558;
6. e) C. Bolm, J. P. Hildebrand, K. Muniz, N. Hermanns, Angew. Chem. 2001, 113, 3382; Angew. Chem. Int. Ed. 2001, 40, 3284.
7. e) C. Bolm, J. P. Hildebrand, K. Muniz. N. Hermanns, Angew. Chem. 2001, 113, 3382; Angew. Chem. Int. Ed. 2001, 40, 3284.
8. a) L. Pu, Chem. Rev. 1998, 98, 2405; for leading representative research, see
9. b) M. Irie, T. Yorozu, K. Hayashi, J. Am. Chem. Soc. 1978, 100, 2236;
10. c) T. D. James, K. R. A. S. Sandanayke, S. Shinkai, Nature 1995, 374, 345;
11. d) K. Akagi, G. Piao, S. Kaneko, K. Sakamaki, H. Shirakawa, M. Kyotani, Sciences 1998, 282, 1683;
12. e) L. Zheng, R. C. Urian, Y. Liu, A. K. Y. Jen, L. Pu, Chem. Mater. 2000, 12, 13;
13. f) V. Pugh, Q. S. Hu, L. Pu, Angew. Chem. 2000, 112, 3784; Angew. Chem. Int. Ed. 2000, 39, 3638;
14. f) V. Pugh, Q. S, Hu, L. Pu, Angew. Chem. 2000, 112, 3784; Angew. Chem. Int. Ed. 2000, 39, 3638;
15. g) L. Z. Gong, Q. S. Hu, L. Pu, J. Org. Chem. 2001, 66, 2358;
16. h) J. Lin, Q. S. Hu, M. H. Xu, L. Pu, J. Am. Chem. Soc. 2002, 124, 2088;
17. i) Y. Cui, O. R. Evans, H. L. Ngo, P. S. White, W. B. Lin, Angew. Chem. 2002, 114, 1207; Angew. Chem. Int. Ed, 2002, 41, 1159.
18. i) Y. Cui, O. R. Evans, H. L. Ngo, P. S. White, W. B. Lin, Angew. Chem. 2002, 114, 1207; Angew. Chem. Int. Ed, 2002, 41, 1159.
19. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
20. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
21. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
22. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
23. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
24. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
25. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
26. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
27. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
28. For resolution of binaphthols, see a) B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397; b) F. Toda, K. Tanaka, J. Org. Chem. 1988, 53, 3607; c) S. Miyano, K. Kawahara, Y. Inoue, H. Hashimoto, Tetrahedron Lett. 1987, 28, 355; d) W. H. Pirkle, J. L. Schreiner, J. Org. Chem. 1981, 46, 4988; e) Q. S. Hu, D. Vitharana, L. Pu, Tetrahedron: Aymmetry 1995, 6, 2123; f) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for nonoxidative syntheses of chiral binaphthyl, see g) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153; h) M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732; i) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723; j) J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
29. a) M. Nakajima, I. Miyoshi, K. Kanayama, S.-I. Hashimoto, J. Org. Chem. 1999, 64, 2264;
30. b) X. Lin, J. Yang, M. C. Kozlowski, Org. Lett. 2001, 3, 1137. and references therein.
31. R. Irie, K. Masutani, T Katsuki, Synlett 2000, 1433.
32. a) C. Y. Chu, D. R. Hwang, S. K. Wang, B. J. Uang, Chem. Commun. 2001, 980;
33. b) S. W. Hon, C. H. Li, J. H. Kuo, N. B. Barhate, Y. H. Liu, Y. Wang, C. T. Chen, Org. Lett. 2001, 3, 869.
34. Z. Luo, Q. Liu, L. Gong, X. Cui, A. Mi, Y. Jiang, Chem. Commun. 2002, 914.
35. H. C. Zhang, W. S. Huang, L. Pu, J. Org. Chem. 2001, 66, 481.
36. For applications of a similar strategy in other reactions, see a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; b) T. Ooi, Y. Uemastu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621; Angew. Chem. Int. Ed. 2002, 41, 1551; c) K. Mikami, K. Aikawa, Y. Yusa, Org. Lett. 2002, 4, 95.
37. For applications of a similar strategy in other reactions, see a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; b) T. Ooi, Y. Uemastu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621; Angew. Chem. Int. Ed. 2002, 41, 1551; c) K. Mikami, K. Aikawa, Y. Yusa, Org. Lett. 2002, 4, 95.
38. For applications of a similar strategy in other reactions, see a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; b) T. Ooi, Y. Uemastu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621; Angew. Chem. Int. Ed. 2002, 41, 1551; c) K. Mikami, K. Aikawa, Y. Yusa, Org. Lett. 2002, 4, 95.
39. For applications of a similar strategy in other reactions, see a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; b) T. Ooi, Y. Uemastu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621; Angew. Chem. Int. Ed. 2002, 41, 1551; c) K. Mikami, K. Aikawa, Y. Yusa, Org. Lett. 2002, 4, 95.
40. For applications of a similar strategy in other reactions, see a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; b) T. Ooi, Y. Uemastu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621; Angew. Chem. Int. Ed. 2002, 41, 1551; c) K. Mikami, K. Aikawa, Y. Yusa, Org. Lett. 2002, 4, 95.
41. a) L. J. Theriot, G. O. Carlisle, H. J. Hu, J. Inorg. Nucl. Chem. 1969, 31, 2841;
42. b) J. J. R. Frausto da Silva, R. Wootton, R. D. Gillard, J. Chem. Soc. A 1970, 3369.