Synthesis of Chiral 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) via a Novel Nickel-Catalyzed Phosphine Insertion

Journal of Organic Chemistry

Volumn 59, Issue 23, 1994, Pages 7180-7181

  Cai, Dongwei ^a   Payack, Joseph F ^a   Bender, Dean R ^a   Hughes, David L ^a   Verhoeven, Thomas R ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751157286     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00102a059     Document Type: Note

References (33)

1. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
2. Toriumi, K.; Ito, T.; Takaya, H.; Souchi, T.; Noyori, R. Acta Crystallogr. Sect. B: Struct. Sci. 1982, B32, 807.
3. Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245
4. Ojima, I. Catalytic Asymmetric Synthesis, VCH: New York, New York, 1993.
5. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1994
6. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
7. Takaya, H.; Akutaguwa, S.; Noyori, R. Org. Synth. 1989, 67, 20
8. Kawashima, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993, 66, 2002.
9. Tanaka, K.; Okada, T.; Toda, F. Angew. Chem. Int. Ed. Engl. 1993, 32, 1147.
10. Toda, F.; Tanaka, K. J. Org. Chem. 1988,53, 3607.
11. Dolle, R. E.; Schimidt, S. J.; Kruse, L. I. J. Chem. Soc., Chem. Commun. 1987, 904.
12. Vondenhof, M.; Mattay, J. Tetrahedron Lett. 1990, 31, 985
13. Kurz, L.; Lee, G.; Morgans, D., Jr.; Waldyke, M. J.; Ward, T. Tetrahedron Lett. 1990, 31, 6321.
14. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945
15. Aguiar, A. M.; Greenberg, H. J.; Rubenstein K. E. J. Org. Chem. 1963, 28, 2091
16. Imamoto, T.; Oshiki, Onozawa, T.; Kusumoto, T.; Sato, K. J.Am. Chem. Soc. 1990,112, 5244.
17. Imamoto, T. Pure Appl. Chem. 1993, 65, 655
18. Tamao, K.; Kumada, M. The Chemistry of the Metal-Carbon Bond, V4; John Wiley & Sons Ltd.: New York, New York, 1987: pp 820-887
19. Cassar, L.; Foà, M. J. Organomet. Chem. 1974, 74, 75.
20. Morvillo, A.; Turco, A. J. Organomet. Chem. 1982, 224, 387.
21. Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267
22. Parshall, G. W. J. Am. Chem. Soc. 1974, 96, 2360.
23. Otsuka, S.; Nakamura, A.; Yoshida, T.; Naruto, M.; Ataka, K. J. Am. Chem. Soc. 1973, 95, 3180
24. Braterman, P. S.; Cross, R. J.; Yong, G. B. J. Chem. Soc. Dalton Trans. 1976, 1306.
25. Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1977, 99, 844
26. Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177
27. Ohta, T.; Ito, M.; Inagaki, K.; Takaya, H. Tetrahedron Lett. 1993, 34, 1615
28. Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908.
29. Semmelhack, M. F.; Helquist, P.; Jones, L. D.; Keller, L.; Mendelson, L.; Ryono, L. S.; Smith, J. G.; Stauffer, R. D. J. Am. Chem. Soc. 1981, 103, 6460
30. Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979,101, 7548.
31. Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organomet. 1983, 2, 1467.
32. Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980,102, 4933
33. The Aldrich Library of 13C and 1H FT NMR Spectra; Aldrich: Milwaukee, WI, 1993; Vol. 2, p 1663