General synthetic route to chiral flexible biphenylphosphine ligands: The use of a chiral additive enables the preparation and observation of metal complexes incorporating the enantiopure form

Organic Letters

Volumn 3, Issue 2, 2001, Pages 243-245

  Mikami, Koichi ^a   Aikawa, Kohsuke ^a   Korenaga, Toshinobu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

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ARTICLE;

EID: 0000815289     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0068896     Document Type: Article

References (25)

1. (a) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis, Vol. 1-3; Springer: Berlin, 1999.
2. (b) Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Ed.; VCH: Weiheim, 1998.
3. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. (d) Brunner, H.; Zettlmeier, W. Handbook of Enantio-selective Catalysis; VCH: Weiheim, 1993.
5. (e) Catalytic Asymmetric Synthesis, Vol. I and II; Ojima, I., Ed.; VCH: New York, 1993: p 2000.
6. (f) Kagan, H. B. Comprehensive Organic Chemistry, Vol. 8; Pergamon: Oxford, 1992.
7. (g) Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff Publishers: Dordrecht, 1986.
8. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059.
9. BIPHEP was named after 6,6′-substituted MeO-BIPHEP. (a) Schmid, R.; Broger, E.; A. Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem. 1996, 68, 131-138.
10. (b) Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315-6323, and references therein.
11. (a) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497.
12. (b) Review on asymmetric activation: Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Ueki, M.; Angelaud, R. Angew. Chem., Int. Ed. 2000, 39, 3532-3556. Also see highlights of conformational control of ligand: Muñiz, K.; Bolm, C. Chem. Eur. J. 2000, 6, 2309-2316.
13. (b) Review on asymmetric activation: Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Ueki, M.; Angelaud, R. Angew. Chem., Int. Ed. 2000, 39, 3532-3556. Also see highlights of conformational control of ligand: Muñiz, K.; Bolm, C. Chem. Eur. J. 2000, 6, 2309-2316.
14. (a) BPBP was also termed for this bisphosphine ligand but synthesized unsuccessfully to give the monophosphine, 5-phenyldibenzophospholane: Uehara, A.; Bailar, J. C., Jr. J. Organomet. Chem. 1982, 239, 1-10. See also: Miyamoto, T. K.; Matsuura, Y.; Okude, K.; Ichida, H.; Sasaki, Y. J. Organomet. Chem. 1989, 373, C8-C12.
15. (a) BPBP was also termed for this bisphosphine ligand but synthesized unsuccessfully to give the monophosphine, 5-phenyldibenzophospholane: Uehara, A.; Bailar, J. C., Jr. J. Organomet. Chem. 1982, 239, 1-10. See also: Miyamoto, T. K.; Matsuura, Y.; Okude, K.; Ichida, H.; Sasaki, Y. J. Organomet. Chem. 1989, 373, C8-C12.
16. (b) Bennett, M. A.; Bhargava, S. K.; Griffiths, K. D.; Robertson, G. B. Angew. Chem., Int. Ed. Engl. 1987, 26, 260-261.
17. (c) Desponds, O.; Schlosser, M. J. Organomet. Chem. 1996, 507, 257-261.
18. (d) Desponds, O.; Schlosser, M. Tetrahedron Lett. 1996, 37, 47-48.
19. (a) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180-7181.
20. (b) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Org. Synth. 1998, 6-11.
21. Synthesis of MOP ligand: Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945-1948.
22. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779-1787.
23. Zhang, W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371-3380.
24. 1H NMR spectra. (R)-8a/ (R)-9: δ 4.04 (d, 9.3 Hz, 2H, amino proton), 4.78 (d, 9.3 Hz, 2H, amino proton).
25. 2[(R)-binap][(R)-dmdabn]: Mikami, K.; Korenaga, T.; Ohkuma, T.; Noyori, R. Angew. Chem., Int. Ed. 2000, 39, 3707-3710.