Enantioselective catalysis XVI: Regio- and enantioselectivity in nickel-catalysed cross-coupling reactions of allylic substrates with Grignard reagents

Inorganica Chimica Acta

Volumn 269, Issue 1, 1998, Pages 34-42

  Nagel, Ulrich ^a   Nedden, Hans Günter ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Cross coupling; Enantioselective catalysis; Nickel catalysed Grignard reagents

Indexed keywords

ALKALINITY; CATALYSIS; CATALYSTS; CHEMICAL BONDS; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; LIGANDS; LIQUID CHROMATOGRAPHY; MAGNESIUM COMPOUNDS; PALLADIUM COMPOUNDS; REAGENTS; STEREOCHEMISTRY;

ASYMMETRIC SYNTHESIS; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; ENANTIOMERIC COMPOSITION; ENANTIOSELECTIVE CATALYSIS; ENANTIOSELECTIVE CATALYSTS; GAS-LIQUID CHROMATOGRAPHY; GRIGNARD REAGENT;

NICKEL COMPOUNDS;

EID: 0008461536     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0020-1693(97)05770-8     Document Type: Article

References (43)

1. V. Farina, in L.J. Hegedus (ed.), Comprehensive Organometallic Chemistry II, Vol. 12, Elsevier, Oxford, 1995, Ch. 3.4.
2. U. Nagel and B. Rieger, Organometallics, 8 (1989) 1534.
3. U. Nagel and A. Bublewitz, Chem. Ber., 125 (1992) 1061; U. Nagel and T. Krink, Angew. Chem., 105 (1993) 1099; Angew. Chem., Int. Ed. Engl., 32 (1993) 1052.
4. U. Nagel and A. Bublewitz, Chem. Ber., 125 (1992) 1061; U. Nagel and T. Krink, Angew. Chem., 105 (1993) 1099; Angew. Chem., Int. Ed. Engl., 32 (1993) 1052.
5. U. Nagel and A. Bublewitz, Chem. Ber., 125 (1992) 1061; U. Nagel and T. Krink, Angew. Chem., 105 (1993) 1099; Angew. Chem., Int. Ed. Engl., 32 (1993) 1052.
6. T. Hayashi, in I. Ojima (ed.), Catalytic Asymmetric Synthesis, VCH, Weinheim, 1993, Ch. 7.1; M. Kumada and K. Tamao, in F.R. Hartley (ed.), The Chemistry of Metal-Carbon Bond, Vol. 4, Wiley, New York, 1987, Ch. 9.
7. T. Hayashi, in I. Ojima (ed.), Catalytic Asymmetric Synthesis, VCH, Weinheim, 1993, Ch. 7.1; M. Kumada and K. Tamao, in F.R. Hartley (ed.), The Chemistry of Metal-Carbon Bond, Vol. 4, Wiley, New York, 1987, Ch. 9.
8. H.R. Sonawane, N.S. Bellur, J.R. Ahuja and D.G. Kulkarni, Tetrahedron: Asymmetry, 3 (1992) 163.
9. U. Nagel and H.G. Nedden, Chem. Ber., 130 (1997) 535.
10. U. Nagel and H.G. Nedden, Chem. Ber., 130 (1997) 989.
11. G. Consiglio and R.M. Waymouth, Chem. Rev., 89 (1989) 257; E. Carmona, P. Palma and M.L. Poveda, Polyhedron, 5 (1990) 757.
12. G. Consiglio and R.M. Waymouth, Chem. Rev., 89 (1989) 257; E. Carmona, P. Palma and M.L. Poveda, Polyhedron, 5 (1990) 757.
13. V.A. Pavlov, E.A. Mistryukov, H. Duddeck, M.G. Vinogradov and G. Snatzke, J. Mol. Catal., 79 (1993) 55.
14. U. Nagel, E. Kinzel, J.G. Andrade and G. Prescher, Chem. Ber., 119 (1986) 3326; E. Kinzel, Ph.D. Thesis, Ludwig Maximilians Universität, Munich, 1985.
15. U. Nagel, E. Kinzel, J.G. Andrade and G. Prescher, Chem. Ber., 119 (1986) 3326; E. Kinzel, Ph.D. Thesis, Ludwig Maximilians Universität, Munich, 1985.
16. U. Nagel and H.G. Nedden, Chem. Ber., 130 (1997) 385.
17. B. Bosnich and P.B. Mackenzie, Pure Appl. Chem., 54 (1982) 189; B.M. Trost and D.L. van Vranken, Chem. Rev., 96 (1996) 395.
18. B. Bosnich and P.B. Mackenzie, Pure Appl. Chem., 54 (1982) 189; B.M. Trost and D.L. van Vranken, Chem. Rev., 96 (1996) 395.
19. G. Schomburg, in M.G. Weller (ed.), Gas Chromatography, A Practical Course, VCH, Weinheim, 1990.
20. H. Römer, personal communication, 1995.
21. R. Benn and H. Günther, Angew. Chem., 95 (1983) 381; Angew. Chem., Int. Ed. Engl., 22 (1983) 390; H. Kessler, M. Gehrke and C. Griesinger, Angew. Chem., 100 (1988) 507; Angew. Chem., Int. Ed. Engl., 27 (1988) 490.
22. R. Benn and H. Günther, Angew. Chem., 95 (1983) 381; Angew. Chem., Int. Ed. Engl., 22 (1983) 390; H. Kessler, M. Gehrke and C. Griesinger, Angew. Chem., 100 (1988) 507; Angew. Chem., Int. Ed. Engl., 27 (1988) 490.
23. R. Benn and H. Günther, Angew. Chem., 95 (1983) 381; Angew. Chem., Int. Ed. Engl., 22 (1983) 390; H. Kessler, M. Gehrke and C. Griesinger, Angew. Chem., 100 (1988) 507; Angew. Chem., Int. Ed. Engl., 27 (1988) 490.
24. R. Benn and H. Günther, Angew. Chem., 95 (1983) 381; Angew. Chem., Int. Ed. Engl., 22 (1983) 390; H. Kessler, M. Gehrke and C. Griesinger, Angew. Chem., 100 (1988) 507; Angew. Chem., Int. Ed. Engl., 27 (1988) 490.
25. F.J. Mc Enroe, C.K. Sha and S.S. Hall, J. Org. Chem., 41 (1976) 3465.
26. H.E. Ramsden, A.E. Balint, W.R. Whithford, J.J. Walburn and R. Cserr, J. Org. Chem., 22 (1957) 1202.
27. J.M. Brown, K.V. Baker, G.D. Hughes, R.J. Taylor, K. Skarnulis and A. Sexton, J. Org. Chem., 56 (1991) 698.
28. A. Yamamoto, T. Yamamoto and J. Ishizu, J. Am. Chem. Soc., 103 (1981) 6863.
29. W.G. Young and S. Winstein, J. Am. Chem. Soc., 57 (1935) 2013.
30. H.L. Goering and R.R. Jacobson, J. Am. Chem. Soc., 80 (1958) 3277.
31. W.C. Still and T.L. Macdonald, J. Org. Chem., 41 (1976) 3620.
32. T. Hayashi, M. Konishi, K. Yokota and M. Kumada, J. Organomet. Chem., 285 (1985) 359.
33. G. Consiglio, M. Scalone and F. Rama, J. Mol. Catal., 50 (1989) L11.
34. T. Hiyama and N. Wakasa, Tetrahedron Lett., 26 (1985) 3259.
35. G. Consiglio, O. Piccolo, L. Roncetti and F. Morandini, Tetrahedron, 42 (1986) 2043.
36. R.M. Magid, E.C. Nieh and R.D. Gandour, J. Org. Chem., 36 (1971) 2099; K.W. Wilson, J.D. Roberts and W.G. Young, J. Am. Chem. Soc., 71 (1949) 2019.
37. R.M. Magid, E.C. Nieh and R.D. Gandour, J. Org. Chem., 36 (1971) 2099; K.W. Wilson, J.D. Roberts and W.G. Young, J. Am. Chem. Soc., 71 (1949) 2019.
38. H. Kurosawa, J. Organomet. Chem., 334 (1987) 243, and Refs. therein.
39. H. Kurosawa, H. Ohnishi, M. Emoto, Y. Kawasaki, S. Murai and I. Ikeda, Organometallics, 9 (1990) 3038, and Refs. therein.
40. P. Heimbach and H. Schenkluhn, Top. Curr. Chem., 92 (1980) 45; P. Heimbach, T. Bartik, I. Gerdes and H.G. Schulte, J. Organomet. Chem., 376 (1989) 359; P. Heimbach, T. Bartik, L. Marko and H.G. Schulte, Chirality, 3 (1991) 324.
41. P. Heimbach and H. Schenkluhn, Top. Curr. Chem., 92 (1980) 45; P. Heimbach, T. Bartik, I. Gerdes and H.G. Schulte, J. Organomet. Chem., 376 (1989) 359; P. Heimbach, T. Bartik, L. Marko and H.G. Schulte, Chirality, 3 (1991) 324.
42. P. Heimbach and H. Schenkluhn, Top. Curr. Chem., 92 (1980) 45; P. Heimbach, T. Bartik, I. Gerdes and H.G. Schulte, J. Organomet. Chem., 376 (1989) 359; P. Heimbach, T. Bartik, L. Marko and H.G. Schulte, Chirality, 3 (1991) 324.
43. H. Felkin, G. Swierczewski, C. Chuit, C. Frajerman and G. Roussi, J. Organomet. Chem., 127 (1977) 371.