Asymmetric Grignard cross-coupling reaction: An investigation of the factors influencing asymmetric induction with a new type of pyrrolidinephosphane

Chemische Berichte

Volumn 130, Issue 4, 1997, Pages 535-542

  Nagel, Ulrich ^a   Nedden, Hans Günter ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Asymmetric amplification; Cross coupling; Gas chromatography; Grignard reactions; Pyrrolidinephosphanes

Indexed keywords

EID: 0000766322     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300414     Document Type: Article

References (33)

1. V. Farina in Comprehensive Organometctllic Chemistry II, vol. 12 (Ed.: L. J. Hegedus), Elsevier Science Ltd. Oxford, New York, Tokyo, 1995, chapter 3.4 and literature cited therein. [2] T. Hayashi in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH Publishers, Weinheim, New York, Cambridge, 1993, Chapter 7.1 and literature cited therein.
2. G. Consiglio, Chimia 1996, 50, 73-78; G. Consiglio, F. Morandini, O. Piccolo, Tetrahedron 1983, 16, 2699-2707.
3. M. Kumada, Pure Appl. Client. 1980, 52, 669-679; M. Kumada, K. Sumitani, K. Tamao, Y. Kiso, J. Am. Cliem. Soc. 1972, 27, 9268-9268.
4. M. Yamashita, A. lida, Bull. Client. Soc. Jptt. 1988, 61, 2365-2367.
5. H. R. Sonawane, N. S. Bellur, J. R. Ahuja, D. G. Kulkarni, Tetrahedron: Asymmetry 1992, 3, 163-192.
6. A. F. Indolese, G. Consielio, J. Organomet. Chem. 1993, 463, 23-27.
7. T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki, M. Kumada, J. Org. Client. 1983, 48, 2195-2202.
8. J U. Nagel, H. G. Nedden, Chem. Ber. 1997, 130, 385-397.
9. J. M. Brown, K. V. Baker, G. D. Hughes, R. J. Taylor, K. Skarnulis, A. Sexton, J. Org. Chem. 1991, 56, 698-702.
10. A. Loupy, B. Tchoubar in Salt Effets in Organic and Organometallic Chemistry, VCH Publishers, Weinheim, New York, Cambridge, 1992, chapter 7.
11. C. Bernadon, J. Organomet. Client. 1989, 367, 11-17; A. M. Egorov, A. V. Anisimov, J. Organomet. Chein. 199-4, 479, 197-198; A. M. Egorov, A. V. Anisimov, J. Organomet. Client. 1995,495, 131-134.
12. H. B. Kasan, J. C. Fiaud in Topics in Stereochemistry, vol. 18, (Eds.: E. L. Eliel, S. H. Wilen), John Wiley & Sons, New York, Chichester, Brisbane, Toronto, Singapore, 1988, 249-313; T. Hayashi, K. Kanehira, T. Hioki, M. Kumada, Tetrahedron Lett. 1981,22, 137-140.
13. P. R. Markies, O. S. Akkermann, F. Bickelhaupt in Advances in Organometallic Chemistry, Vol. 32, Academic Press Inc., San Diego, London, 1991, 147-226.
14. E. Kinzel, Ph. D. Thesis, Ludwig Maximilians Universität, München, 1985.
15. H. Brunner, H. J. Lautenschlaeer, W. A. König, R. Krebber, Client. Ber. 1990,123, 847-853?
16. G. W. Watt, P. S. Gentile, E. P. Helvenston, J. Am. Chein. Soc. 1955, 77, 2752-2753; H. D. Hardt, H. Pohlmann, Z. Anorg. Allg. Chem. 1966, 343, 92-100.
17. Komplexomctrische Beslimmwigsmethoden mit Titriplcx, E. Merck, Darmstadt.
18. J G. G. Schomburg in Gas Chromatograph); A Practical Course (Ed.: M. G. Weller), VCH Publishers, Weinheim, Deerfield Beach Florida, Basel, 1990.
19. W. Keim, A. Köhnes, W. Meltzow, H. Römer, J. High Res. Chroma togr. 1991, 14, 507-529.
20. This separation has application No. CD 215b; H. Römer, personal communication 1995.
21. R. Selke, C. Facklam, H. Foken, D. Heller, Tetrahedron: Asymmetry 1993, 4, 369-382; V. Rautenstrauch, Bull. Soc. Chim. Fr. 1994, 131, 515-524.
22. J. M. Brown, N. A. Cooley, K. V. Baker, G. D. Hughes, R. J. Taylor, J. Organomet. Client. 1989, 370, 397-406; J. M. Brown, N. A. Cooley, J. Chem. Soc., Chem. Commun. 1988, 1345-1347.
23. H. Felkin, G. Swierczewski, Tetrahedron 1975, 31, 2735-2748.
24. M. Kumada, K. Tamao in The Chemistry of Metal-Carbon Bonds, vol. 4 (Ed.: F. R. Hartley), John Wiley & Sons, New York, Chichester, Birsbane, Toronto, Singapore, 1987, chapter 9; R. M. Kellogg, G. A. Cross, J. Clicm. Soc.. Chein. Commun. 1987, 1746-1747; R. M. Kellogg, G. A. Cross, B. K. Vriesema, G. Boven, F. Van Bolhuis, J. "Organomet. Chem. 1989, 370, 357-381.
25. R. Noyori, M. Kitamura, Angew. Chem. 1991,103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69.
26. Zn: R. Noyori, M. Kitamura, S. Suga, M. Niwa, J. Am. Chem. Soc. 1995, 777,4832-4842; C. Bolm, G. Schlingloff, K. Harms, Chem. Der. 1992, 725, 1191-1203. - Ni: C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 725, 1205-1215; A. H. M. de Vries, J. F. G. Jansen, B. L. Feringa, Tetrahedron 1994,50,4479-4491. - Ti: K. Mikami, Pure Appl. Chem. 1996, 68, 639-644; M. Hayashi, T. Matsuda, N. Oguni, J. Chem. Soc., Perkin Trans, l 1992, 3135-3140.
27. H. B. Kagan, S. H. Zhao, O. Samuel, D. Rainford, D. Guillaneux, J. Am. Chem. Soc. 1994, 776, 9430-9439; H. B. Kagan, C. Girard, D. Guillaneux, D. Rainford, O. Samuel, S. Y. Zhang, S. H. Zhao, Acta Chem. Scand. 1996, 50, 345-352.
28. P. Heimbach, H. Schenkluhn, Top. Ctirr. Chem. 1980, 92, 45-108.
29. A Yamamoto, K. Tatsumi, R. Hoffmann, J. K. Stille, Bull. Chem. Soc. Jpn. 1981, 54, 1857-1867; A. Yamamoto, T. Yamamoto, K. Tatsumi, S. Komiya, A. Nakamura, J. Am. Chem. Soc. 1984,106, 8181-8188; A. Yamamoto, T. Yamamoto, F. Osawa, Pure Appl. Chem. 1984, 56, 1621-1634; A. Yamamoto, T. Yamamoto, F. Osawa, Pure Appl. Chem. 1985, 57, 1799-1808.
30. J. M. Brown, N. A. Cooley, Chem. Rev: 1988, 88, 1031-1046;
31. J. M. Brown, P. J. Guiry, Inorg. Chim. Acta 1994,220, 249-259.
32. P. G. T. Foga, J. D. Lambert, Proc. R. Soc. London, Ser. A. 1955, 252, 537-538.
33. SHELXTL V5.03, Siemens Analytical X-Ray Instruments Inc., 1995.