Novel axial chiral catalyst derived from biphenyl ligand bearing only two ortho-substituents

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2681-2684

  Imai, Yoshitane ^a   Zhang, Wanbin ^a   Kida, Toshiyuki ^a   Nakatsuji, Yohji ^a   Ikeda, Isao ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; CYCLOPROPANE DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030907799     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00428-0     Document Type: Article

References (30)

1. Reported as a poster presentation at Osaka University, 43rd Symposium on Organometallic Chemistry, Japan, October 31-November 1, 1996, Abstracts, 106-107.
2. For reviews: (a) Tongi, A.; Venanzi, L. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 497-526.
3. (b) Pfaltz, A. ACC. Chem. Res. 1993, 26, 339-345.
4. (c) Doyole, M. P. Catalytic Asymmetric Synthesis. (Ed.: Ojima, I.), VCH publishers, New York, 1993, p63.
5. (d) Bolm, C. Angew. Chem. Int. Ed. Engl. 1991, 30, 542-543.
6. (a) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron A symmetry 1996, 7, 2453-2462. This kind of ligands was also reported independently by the Andersson and the Knight groups, see:
7. (b) Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1996, 37, 4073-4076.
8. Harm, A. M.; Knight, J. G.; Stemp, G. Synlett 1996, 677-678.
9. (a) Zhang, W.; Adachi, Y.; Hirao, T.; Ikeda, I. Tetrahedron Asymmetry 1996, 7, 451-460.
10. (b) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545-4548.
11. Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995-7998.
12. During our study on this work, two related ligands prepared from chiral biaryl and racemic biaryl were reported by the Corey and the Hayashi groups, but one of them needs the resolution of the biaryl material and the other needs the separation of the two diastereomers of the ligand; only one of the two diastereomers shows high enantioselectivity in both situations. See: (a) Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745-8748.
13. (b) Uozumi, Y.; Kyola, H.; Kishi, E.; Kitayama, K.; Hayashi, T. Tetrahedron Asymmetry 1996, 7, 1603-1606.
14. (a) Meyers, A. I.; Meier, A.; Rawson, D. Tetrahedron Lett. 1992, 33, 853-856.
15. (b) Rawson,D.; Meyers, A. I. J. Chem. Soc., Chem. Commun. 1992, 494-496.
16. (c) Mayers, A. I.; Himmelsbach, R. J. J. Am. Chem. Soc. 1985, 107, 682-685.
17. (a) Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis, 1992, 503-517.
18. (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590.
19. -1) 1657(C=N).
20. 3).
21. -1) 1655(C=N).
22. 3).
23. +).
24. +).
25. Selected papers: (a) Tokunoh, R.; Tomiyama, H.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 2449-2452.
26. (b) Pique, C.; Fähndrich, B.; Pfaltz, A. Synlett 1995, 491-492.
27. (c) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 430-432.
28. (d) Fritschi, H.; Leutenegger, U.; Pfaltz, A. Helv. Chim. Acta 1988, 71, 1553-1565.
29. 6 These results also support the assignment of our complex to 5-(S,S,S) with which higher ee was attained.
30. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728.