Palladium-catalyzed asymmetric allylic substitution with a cyclopentadienide: Asymmetric synthesis of metallocenes

Tetrahedron Asymmetry

Volumn 14, Issue 4, 2003, Pages 511-515

  Suzuka, Toshimasa ^a   Kawatsura, Motoi ^a   Okada, Atsushi ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUND; CYCLOPENTADIENIDE; DIOXANE; IRON; METALLOCENE; PALLADIUM; TITANIUM; UNCLASSIFIED DRUG; ZIRCONIUM;

ALLYLATION; ARTICLE; CATALYSIS; CHIRALITY; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 0037458694     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00862-5     Document Type: Article

References (40)

1. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
2. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
3. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
4. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
5. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
6. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
7. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
8. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
9. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
10. For reviews: (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144; (b) Tsuji, J. Pure Appl. Chem. 1982, 54, 197; (c) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp. 799-938; (d) Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press: New York, 1985; (e) Tsuji, J. J. Organomet. Chem. 1986, 300, 281; (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140; (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257; (h) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: New York, 1990; (i) Godleski, S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4; pp. 585-659; (j) Tsuji, J. Palladium Reagents and Catalysts, John Wiley and Sons: Chichester, 1995.
11. For reviews: (a) Trost, B. M.; Chulbom, L. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000, p. 593; (b) Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Vol. 2, Chapter 24; (c) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395; (d) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 325; (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
12. For reviews: (a) Trost, B. M.; Chulbom, L. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000, p. 593; (b) Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Vol. 2, Chapter 24; (c) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395; (d) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 325; (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
13. For reviews: (a) Trost, B. M.; Chulbom, L. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000, p. 593; (b) Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Vol. 2, Chapter 24; (c) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395; (d) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 325; (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
14. For reviews: (a) Trost, B. M.; Chulbom, L. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000, p. 593; (b) Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Vol. 2, Chapter 24; (c) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395; (d) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 325; (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
15. For reviews: (a) Trost, B. M.; Chulbom, L. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000, p. 593; (b) Pfaltz, A.; Lautens, M. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Vol. 2, Chapter 24; (c) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395; (d) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p. 325; (e) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
16. Suzuka T., Ogasawara M., Hayashi T. J. Org. Chem. 67:2002;3355.
17. For reviews on chiral ferrocene derivatives, see: (a) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377; (b) Hayashi, T. Ferrocenes; Togni, A.; Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp. 105-142.
18. For reviews on chiral ferrocene derivatives, see: (a) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377; (b) Hayashi, T. Ferrocenes; Togni, A.; Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp. 105-142.
19. For examples of chiral zirconocenes and titanocenes: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Halterman, R. L. Chem. Rev. 1992, 92, 965; (c) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermühle, D.; Krüger, C.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590; (d) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139.
20. For examples of chiral zirconocenes and titanocenes: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Halterman, R. L. Chem. Rev. 1992, 92, 965; (c) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermühle, D.; Krüger, C.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590; (d) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139.
21. For examples of chiral zirconocenes and titanocenes: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Halterman, R. L. Chem. Rev. 1992, 92, 965; (c) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermühle, D.; Krüger, C.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590; (d) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139.
22. For examples of chiral zirconocenes and titanocenes: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Halterman, R. L. Chem. Rev. 1992, 92, 965; (c) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermühle, D.; Krüger, C.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590; (d) Bell, L.; Whitby, R. J.; Jones, R. V. H.; Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139.
23. Hoveyda A.H., Morken J.P. Angew. Chem., Int. Ed. Engl. 35:1996;1262.
24. Morken J.P., Didiuk M.T., Hoveyda A.H. J. Am. Chem. Soc. 115:1993;6997.
25. Kondakov D.Y., Negishi E. J. Am. Chem. Soc. 118:1996;1577.
26. Wipf P., Ribe S. Org. Lett. 2:2000;1713.
27. Fiaud J.C., Malleron J.L. Tetrahedron Lett. 21:1980;4437.
28. Fiaud J.C., Legros J.Y. J. Org. Chem. 52:1987;1907.
29. Nyström J.E., Vägberg J.O., Söderberg B.C. Tetrahedron Lett. 32:1991;5247.
30. Only one report has appeared on the allylic alkylation of a cyclopentadienide in the presence of a chiral ligand, but the enantioselectivity is not described: Fiaud J.C., Malleron J.L. Tetrahedron Lett. 22:1981;1399.
31. Sprinz J., Helmchen G. Tetrahedron Lett. 34:1993;1769.
32. Matt P., Pfaltz A. Angew. Chem., Int. Ed. Engl. 32:1993;566.
33. Dawson G.J., Frost C.G., Williams J.M.J., Coote S.J. Tetrahedron Lett. 34:1993;3149.
34. For reviews: (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336; (b) Helmchen, G. J. Organomet. Chem. 1999, 576, 203; (c) Williams, J. M. J. Synlett 1996, 705.
35. For reviews: (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336; (b) Helmchen, G. J. Organomet. Chem. 1999, 576, 203; (c) Williams, J. M. J. Synlett 1996, 705.
36. For reviews: (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336; (b) Helmchen, G. J. Organomet. Chem. 1999, 576, 203; (c) Williams, J. M. J. Synlett 1996, 705.
37. Helmchen studied reaction mechanism of the asymmetric allylic alkylation with dimethyl malonate by use of this type of a cationic π-allylpalladium complex: (a) Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2108; (b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523.
38. Helmchen studied reaction mechanism of the asymmetric allylic alkylation with dimethyl malonate by use of this type of a cationic π-allylpalladium complex: (a) Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2108; (b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523.
39. Jaquith J., Guan J., Wang S., Collins S. Organometallics. 14:1995;1079.
40. Hayashi T., Yamamoto A., Ito Y., Nishioka E., Miura H., Yanagi K. J. Am. Chem. Soc. 111:1989;6301.