A facile synthesis of 3 or 3,3′-substituted binaphthols and their applications in the asymmetric addition of diethylzinc to aldehydes

Journal of Organometallic Chemistry

Volumn 691, Issue 6, 2006, Pages 1282-1287

  Guo, Qun Sheng ^a   Lu, Yong Na ^a   Liu, Bing ^a   Xiao, Jian ^a   Li, Jin Shan ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; BINOL; Lithiation; Quinoline

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; AROMATIC COMPOUNDS; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL);

ASYMMETRIC CATALYSIS; BINOL; LITHIATION; QUINOLINE;

NITROGEN COMPOUNDS;

EID: 32544459409     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.12.042     Document Type: Article

References (26)

1. L. Pu Chem. Rev. 98 1998 2405 2494
2. Y. Chen, S. Yekta, and A.K. Yudin Chem. Rev. 103 2003 3155 3211
3. P. Kočovskú, S. Vyskočil, and M. Smrčina Chem. Rev. 103 2003 3213 3245
4. J.M. Brunel Chem. Rev. 105 2005 857 897
5. D.S. Lingenfelter, R.C. Helgeson, and D.J. Cram J. Org. Chem. 46 1981 393 406
6. P.J. Cox, W. Wang, and V. Snieckus Tetrahedron Lett. 33 1992 2253 2256
7. C. Qian, C. Zhu, and T. Huang J. Chem. Soc., Perkin Trans. I 1998 2131 2132
8. K.B. Simonsen, K.V. Gothelf, and K.A. Jørgensen J. Org. Chem. 63 1998 7536 7538
9. H. Kodama, J. Ito, K. Hori, T. Ohta, and I. Furukawa J. Organomet. Chem. 603 2000 6 12
10. X.L. Bai, X.D. Liu, M. Wang, C.Q. Kang, and L.X. Gao Synthesis 2005 458 464
11. D.S. Lingenfelter, R.C. Helgeson, and D.J. Cram J. Org. Chem. 46 1981 393 406
12. J. Li, W.D. Li, Y. Li, Y.L. Li, and S.Y. Yang Org. Prep. Proced. Int. 27 1995 685 690
13. M.T. Reetz, J.A. Ma, and R. Goddard Angew. Chem., Int. Ed. Engl. 44 2005 412 415
14. H. Kitajima, Y. Aoki, K. Ito, and T. Katsuki Chem. Lett. 1995 1113 1114
15. The reactions of lithiated derivative of thiophene and m-trifluoromethylphenyl bromide were reported: H. Gilman, and L.A. Woods J. Am. Chem. Soc. 66 1944 1981 1982
16. H. Gilman, and D.A. Shirley J. Am. Chem. Soc. 71 1949 1870 1871
17. 2 = 0.1307, GOF = 1.003.
18. Y. Chen, S. Yekta, L.J.P. Martyn, J. Zheng, and A.K. Yudin Org. Lett. 2 2000 3433 3436
19. M. Mori, and T. Nankai Tetrahedron Lett. 38 1997 6233 6236
20. D.R. Williams, and M.G. Fromhold Synlett 1997 523 524
21. F.Y. Zhang, and A.S.C. Chan Tetrahedron: Asymmetry 8 1997 3651 3655
22. M. Kitamura, S. Suga, K. Kawai, and R. Noyori J. Am. Chem. Soc. 108 1986 6071 6072
23. M. Watanabe, S. Araki, Y. Butsugan, and M. Uemura J. Org. Chem. 56 1991 2218 2224
24. P.A. Chaloner, and S.A.R. Perena J. Chem. Soc., Perkin Trans. I. 1991 2731 2735
25. M. Ishizaki, K. Fujita, M. Shimamoto, and O. Hoshino Tetrahedron: Asymmetry 5 1994 411 424
26. A. Smaardijk, and H. Wynberg J. Org. Chem. 52 1987 135 137