Facile preparation of optically pure 7,7′-disubstituted BINOLS and their application in asymmetric catalysis

Journal of Organic Chemistry

Volumn 68, Issue 20, 2003, Pages 7921-7924

  Liu, Quan Zhong ^a,b   Xie, Nan Sheng ^b   Luo, Zhi Bin ^a   Cui, Xin ^a   Cun, Lin Feng ^a   Gong, Liu Zhu ^a   Mi, Ai Qiao ^a   Jiang, Yao Zhong ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b Sichuan Teachers College   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSTS; OXIDATION;

SUZUKI COUPLING;

AROMATIC COMPOUNDS;

2,2' DIHYDROXY 1,1' DINAPHTHYL DERIVATIVE; NAPHTHOL DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; OPTICAL ROTATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0141653954     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034831+     Document Type: Article

References (44)

1. For reviews, see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. (b) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
3. (c) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999.
4. (d) Jorgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558.
5. (e) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284.
6. For reviews, see: (a) Pu, L. Chem. Rev. 1998, 98, 2405.
7. For leading representative research see: (b) Irie, M.; Yorozu, T.; Hayashi, K. J. Am. Chem. Soc. 1978, 100, 2236.
8. (c) James, T. D.; Sandanayke, K. R. A. S.; Shinkai, S. Nature 1995, 374, 345.
9. (d) Akagi, K.; Piao, G.; Kaneko, S.; Sakamaki, K.; Shirakawa, H.; Kyotani, M. Sciences 1998 282, 1683.
10. (e) Zheng, L.; Urian, R. C.; Liu, Y.; Jen, A. K. Y.; Pu, L. Chem. Mater. 2000, 12, 13.
11. (f) Pugh, V. J.; Hu, Q. S.; Pu, L Angew. Chem., Int. Ed. 2000, 39, 3638.
12. (g) Gong, L. Z.; Hu, Q. S.; Pu, L. J. Org. Chem. 2001, 66, 2358.
13. (h) Lin, J.; Hu, Q. S.; Xu, M. H.; Pu, L. J. Am. Chem. Soc. 2002, 124, 2088.
14. (i) Cui, Y.; Evans, O. R.; Ngo, H. L.; White, P. S.; Lin, W. B. Angew. Chem., Int. Ed. 2002, 41, 1159.
15. Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223 and the references therein.
16. (a) Lee, S. J.; Hu, A.; Lin W. J. Am. Chem. Soc. 2002, 124, 12948.
17. (b) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
18. (c) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793 and references therein.
19. For asymmetric synthesis from the chiral pool: (a) Lipshutz, B. H.; Shin, Y. J. Tetrahedron Lett. 2000, 41, 9515.
20. (b) Lipshutz, B. H.; Shin, Y. J. Tetrahedron Lett. 1998, 39, 7017.
21. For asymmetric catalytic coupling of 7-subsituted naphthols see: (c) Mulrooney, C. A.; Li, X.; DiVirgilio, E. S.; Kozlowski, M. C. J. Am. Chem. Soc. 2003, 125, 6856.
22. (d) Chu, C. Y.; Hwang, D. R.; Wang, S. K.; Uang, B. J. Chem. Commun. 2001, 980.
23. (e) Hon, S. W.; Li, C. H.; Kuo, J. H.; Barhate, N. B.; Liu, Y. H.; Wang, Y.; Chen, C. T. Org. Lett. 2001, 3, 869.
24. (f) Luo, Z.; Liu, Q.; Gong, L.; Mi, A.; Cui, X.; Jiang, Y. Chem. Commun. 2002, 914.
25. (g) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-i. J. Org. Chem. 1999, 64, 2264.
26. (h) Li, X.; Yang, J.; Kozlowski, M. C. Org. Lett. 2001, 3, 1137.
27. For resolution see: (i) Bandin, M.; Casolari, S.; Cozzi, P. G.; Proni, G.; Schmohel, E.; Spada, G. P.; Tagliavini, E.; Umani-Ronchi, A. Eur. J. Org. Chem. 2000, 491.
28. (j) Reeder, J.; Castro, P. P.; Knobler, C. B.; Martinborough, E.; Owens, L.; Diederich, F. J. Org. Chem. 1994, 59, 3151.
29. Luo, Z.; Liu, Q.; Gong, L.; Mi, A.; Cui, X.; Jiang, Y. Angew. Chem., Int. Ed. 2002, 41, 4532.
30. (a) Beugelmans, R.; Bourdet, S.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 4349.
31. (b) Smith, A. B., III; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092.
32. (c) Vutukuri, D. R.; Bharathi, P.; Yu, Z.; Rajasekaran, K.; Tran, M.-H.; Thayumanavan, S. J. Org. Chem. 2003, 68, 1146.
33. (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
34. (b) Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
35. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
36. (a) Saa, J. M.; Dopico, M.; Martorell, G.; Garcia-Raso, A. J. Org. Chem. 1990, 55, 991.
37. (b) Kurz, L.; Lee, G.; Morgans, D., Jr.; Waldyke, M. J.; Ward, T. Tetrahedron Lett. 1990, 31, 6321.
38. For Ti(IV)-BINOLs catalyzed alkynylzinc addition to aldehydes, see: (a) Moore, D.; Pu, L. Org. Lett. 2002, 4, 1855.
39. (b) Gao, G.; Moore, D.; Xie, R. G.; Pu, L. Org. Lett. 2002, 4, 4143.
40. (c) Lu, G.; Li, X.; Chan, A. S. C. Chem. Commun. 2002, 172.
41. (d) Li, X.; Lu, G.; Kwok, W. H.; Chan, A. S. C. J. Am. Chem. Soc. 2002, 124, 12636.
42. For Zn(II) catalyzed alkynyl zinc addition to aldehydes, see: (e) Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373.
43. (f) Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
44. (g) Xu, M.; Pu, L. Org. Lett. 2002, 4, 4555.