Synthesis and Resolution of 2,2'-bis-diphenylphosphino [3,3']biindolyl ; a New Atropisomeric Ligand for Transition Metal Catalysis

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 285-292

  Berens, Ulrich ^a,b   Brown, John M ^a   Long, James ^a   Selke, Rüdiger ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030032246     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00447-5     Document Type: Article

References (44)

1. (a) Takaya H.; Akutagawa S.; Noyori R. Org. Synth. 1989, 67, 20.
2. (b) Takaya H.; Mashima K.; Koyano K.; Yagi M.; Kumobayashi H.; Taketomi T.; Akutagawa S.; Noyori R. J. Org. Chem. 1986, 51, 629.
3. Ligand 1a: Jendralla, H.; Li, C.-H.; Paulus, E. Tetrahedron: Asymmetry 1994, 5, 1297; Ligand 1b: Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, P.; Hansen, H.-J. Helv. Chim. Acta 1988, 71, 897. Ligand 2: Zhang, X. Y.; Uemura, T.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Takaya, H. Synlett, 1994, 501; Ligand 3: Brown, J. M.; Hulmes, D. L; Guiry, P. J. Tetrahedron , 1994, 50, 4493; Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc. Chem. Comm., 1993, 1673-1674.
4. Ligand 1a: Jendralla, H.; Li, C.-H.; Paulus, E. Tetrahedron: Asymmetry 1994, 5, 1297; Ligand 1b: Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, P.; Hansen, H.-J. Helv. Chim. Acta 1988, 71, 897. Ligand 2: Zhang, X. Y.; Uemura, T.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Takaya, H. Synlett, 1994, 501; Ligand 3: Brown, J. M.; Hulmes, D. L; Guiry, P. J. Tetrahedron , 1994, 50, 4493; Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc. Chem. Comm., 1993, 1673-1674.
5. Ligand 1a: Jendralla, H.; Li, C.-H.; Paulus, E. Tetrahedron: Asymmetry 1994, 5, 1297; Ligand 1b: Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, P.; Hansen, H.-J. Helv. Chim. Acta 1988, 71, 897. Ligand 2: Zhang, X. Y.; Uemura, T.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Takaya, H. Synlett, 1994, 501; Ligand 3: Brown, J. M.; Hulmes, D. L; Guiry, P. J. Tetrahedron , 1994, 50, 4493; Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc. Chem. Comm., 1993, 1673-1674.
6. Ligand 1a: Jendralla, H.; Li, C.-H.; Paulus, E. Tetrahedron: Asymmetry 1994, 5, 1297; Ligand 1b: Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, P.; Hansen, H.-J. Helv. Chim. Acta 1988, 71, 897. Ligand 2: Zhang, X. Y.; Uemura, T.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Takaya, H. Synlett, 1994, 501; Ligand 3: Brown, J. M.; Hulmes, D. L; Guiry, P. J. Tetrahedron , 1994, 50, 4493; Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc. Chem. Comm., 1993, 1673-1674.
7. Ligand 1a: Jendralla, H.; Li, C.-H.; Paulus, E. Tetrahedron: Asymmetry 1994, 5, 1297; Ligand 1b: Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, P.; Hansen, H.-J. Helv. Chim. Acta 1988, 71, 897. Ligand 2: Zhang, X. Y.; Uemura, T.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Takaya, H. Synlett, 1994, 501; Ligand 3: Brown, J. M.; Hulmes, D. L; Guiry, P. J. Tetrahedron , 1994, 50, 4493; Brown, J. M.; Hulmes, D. I.; Layzell, T. P. J. Chem. Soc. Chem. Comm., 1993, 1673-1674.
8. Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, J. A.; Powell, D. R. J. Am. Chem. Soc , 1992, 114, 10680; Yamamoto, K.; Momose, S.; Funahashi, M.; Ebata, S.; Ohmura, H.; Komatsu, H.; Miyazawa, M. Chem. Lett., 1994, 189.
9. Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, J. A.; Powell, D. R. J. Am. Chem. Soc , 1992, 114, 10680; Yamamoto, K.; Momose, S.; Funahashi, M.; Ebata, S.; Ohmura, H.; Komatsu, H.; Miyazawa, M. Chem. Lett., 1994, 189.
10. Allen, J. V.; Bower, J. F.; Williams, J. Tetrahedron Asymmetry, 1994, 5, 1895; Casalnuovo, A. L.; Rajanbabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem Soc., 1994, 116, 9869; Legros, J. Y.; Fiaud, J. C. Tetrahedron , 1994, 50, 465; Rajanbabu, T. V.; Ayers, T. A. Tetrahedron Lett., 1994, 35, 4295; Rajanbabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101; Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. Engl., 1995, 34, 931-933.
11. Allen, J. V.; Bower, J. F.; Williams, J. Tetrahedron Asymmetry, 1994, 5, 1895; Casalnuovo, A. L.; Rajanbabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem Soc., 1994, 116, 9869; Legros, J. Y.; Fiaud, J. C. Tetrahedron , 1994, 50, 465; Rajanbabu, T. V.; Ayers, T. A. Tetrahedron Lett., 1994, 35, 4295; Rajanbabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101; Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. Engl., 1995, 34, 931-933.
12. Allen, J. V.; Bower, J. F.; Williams, J. Tetrahedron Asymmetry, 1994, 5, 1895; Casalnuovo, A. L.; Rajanbabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem Soc., 1994, 116, 9869; Legros, J. Y.; Fiaud, J. C. Tetrahedron , 1994, 50, 465; Rajanbabu, T. V.; Ayers, T. A. Tetrahedron Lett., 1994, 35, 4295; Rajanbabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101; Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. Engl., 1995, 34, 931-933.
13. Allen, J. V.; Bower, J. F.; Williams, J. Tetrahedron Asymmetry, 1994, 5, 1895; Casalnuovo, A. L.; Rajanbabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem Soc., 1994, 116, 9869; Legros, J. Y.; Fiaud, J. C. Tetrahedron , 1994, 50, 465; Rajanbabu, T. V.; Ayers, T. A. Tetrahedron Lett., 1994, 35, 4295; Rajanbabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101; Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. Engl., 1995, 34, 931-933.
14. Allen, J. V.; Bower, J. F.; Williams, J. Tetrahedron Asymmetry, 1994, 5, 1895; Casalnuovo, A. L.; Rajanbabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem Soc., 1994, 116, 9869; Legros, J. Y.; Fiaud, J. C. Tetrahedron , 1994, 50, 465; Rajanbabu, T. V.; Ayers, T. A. Tetrahedron Lett., 1994, 35, 4295; Rajanbabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101; Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. Engl., 1995, 34, 931-933.
15. Allen, J. V.; Bower, J. F.; Williams, J. Tetrahedron Asymmetry, 1994, 5, 1895; Casalnuovo, A. L.; Rajanbabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem Soc., 1994, 116, 9869; Legros, J. Y.; Fiaud, J. C. Tetrahedron , 1994, 50, 465; Rajanbabu, T. V.; Ayers, T. A. Tetrahedron Lett., 1994, 35, 4295; Rajanbabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101; Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. Engl., 1995, 34, 931-933.
16. Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E. J. Chem. Soc., Chem. Commun. 1995, 685.
17. Synthesis of ligands in this class was commenced during a visit to Oxford between June and September 1994 by Dr. Berens and continued in Rostock and Oxford subsequently. In addition to much of the work described in this paper, racemic 2,2-bis-(diphenylphosphino)-3,3'-di-(benzothiophenyl) was prepared in summer 1994 and subsequently resolved by the method described herein. On learning of the interest of the Milan group we discontinued work on the benzothiophen system; we are grateful to Professor E. Cesarotti for an exchange of information, June-Sept 1995
18. Fraser, R. R.; Bresse, M.; Mansour, T. S. J. Chem. Soc., Chem. Commun., 1983, 620-621; Fraser, R. R.; Mansour, T. S.; Savard, S. Can. J. Chem 1985, 63, 3505-3509; Tupitsyn, I. F.; Popov, A. S.; Shibaev, A. Y. Z. Obshch. Khimii 1992, 62, 2319-2328.
19. Fraser, R. R.; Bresse, M.; Mansour, T. S. J. Chem. Soc., Chem. Commun., 1983, 620-621; Fraser, R. R.; Mansour, T. S.; Savard, S. Can. J. Chem 1985, 63, 3505-3509; Tupitsyn, I. F.; Popov, A. S.; Shibaev, A. Y. Z. Obshch. Khimii 1992, 62, 2319-2328.
20. Fraser, R. R.; Bresse, M.; Mansour, T. S. J. Chem. Soc., Chem. Commun., 1983, 620-621; Fraser, R. R.; Mansour, T. S.; Savard, S. Can. J. Chem 1985, 63, 3505-3509; Tupitsyn, I. F.; Popov, A. S.; Shibaev, A. Y. Z. Obshch. Khimii 1992, 62, 2319-2328.
21. (a) Bergman, J. Acta Chem. Scand. 1971, 25, 1277.
22. (b) Bergman, J.; Eklund, N. Tetrahedron 1980, 6, 1445.
23. (c) Saleha, S.; Khan, N. H.; Siddiqui, A. A.; Kidwai, M. M. Indian J. Chem. 1978, 16B, 122.
24. (d) Hino, T.; Tsuneoka, K.; Nakagawa, M.; Akaboshi, S. Chem. Pharm. Bull. 1969, 17, 550.
25. Sirowej, H.; Khan, S.A.; Plieninger, H. Synthesis 1972, 84.
26. (a) Hlasla, D.J.; Bell, M. R. Heterocycles 1989, 29, 849;
27. (b) Katritzky, A. R.; Lue, P.; Chen, Y.-X. J. Org. Chem. 1990, 55, 3688.
28. (a) Katritzky, A. R.; Akutagawa, K. Tetrahedron Lett. 1985, 26, 5935.
29. (b) Hasan, I.; Marinelli, E. R.; Lin, L-C. C.; Fowler, W. F.; Levy, A. B. J. Org. Chem. 1981, 46, 157.
30. (c) Edwards, M. P.; Doherty, A. M.; Ley, S. V.; Organ, H. M. Tetrahedron 1986, 42, 3723.
31. (d) Somei, M.; Kobayashi, T. Heterocycles 1992, 34, 1295.
32. (e) Gharpure, M.; Stoller, A.; Bellamy, F.; Firnau, G.; Snieckus, V. Synthesis 1991, 1079.
33. (f) Sundberg, R. J.; Russell, H. F. J. Org. Chem. 1973, 38, 3324.
34. Kinast, G.; Tietze, L.-F. Angew. Chem. Int. Ed. Engl. 1976, 15, 239, see also Böhme, H.; Hartke, K. Chem. Ber. 1960, 63, 1305.
35. Kinast, G.; Tietze, L.-F. Angew. Chem. Int. Ed. Engl. 1976, 15, 239, see also Böhme, H.; Hartke, K. Chem. Ber. 1960, 63, 1305.
36. Lowe, G.; Potter, B. J. Chem. Soc., Chem. Commun., 1984, 877-879; Hansen, P. E. Prog. Nucl. Mag. Res. , 1988, 20, 207-255.
37. Lowe, G.; Potter, B. J. Chem. Soc., Chem. Commun., 1984, 877-879; Hansen, P. E. Prog. Nucl. Mag. Res. , 1988, 20, 207-255.
38. Programme gNMR for Apple Macintosh; IvorySoft®1994.
39. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry ,1993, 4, 743-756; Chooi, S.; Tan, M. K.; Leung, P. H.; Mok, K. F. Inorg.Chem., 1994, 33, 3096-3103; Alcock, N.W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc. Chem. Comm., 1995, 395-397.
40. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry ,1993, 4, 743-756; Chooi, S.; Tan, M. K.; Leung, P. H.; Mok, K. F. Inorg.Chem., 1994, 33, 3096-3103; Alcock, N.W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc. Chem. Comm., 1995, 395-397.
41. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry ,1993, 4, 743-756; Chooi, S.; Tan, M. K.; Leung, P. H.; Mok, K. F. Inorg.Chem., 1994, 33, 3096-3103; Alcock, N.W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc. Chem. Comm., 1995, 395-397.
42. Pabel, M.; Willis, A. C.; Wild, S. B. Tetrahedron : Asymmetry, 1995, 6, 2369-74.
43. Leung, P. H.; Willis, A. C.; Wild, S. B. Inorg. Chem., 1992, 31, 1406.
44. Hursthouse, M. D.; Hibbs, D., to be published.