Enantioselective allylic alkylation and amination catalyzed by a chiral P/N ligandpalladium complex

Heterocycles

Volumn 42, Issue 2, 1996, Pages 543-547

  Kubota, Hideki ^a   Koga, Kenji ^b  

^a DAIICHI SANKYO CO   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000961708     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s95     Document Type: Article

References (20)

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3. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566; J. Sprinz and G. Helmchen, Tetrahedron Lett, 1993, 34, 1769; G. J. Dawson, C. G. Frost, J. M. J. Williams, and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149; J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1994, 2065; J. M. Brown, D. I. Hulmes, and P. J. Guiry, Tetrahedron, 1994, 50, 4493; For a mechanistic study, see: J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, and L. Zsolnai, Tetrahedron Lett., 1994, 35, 1523.
4. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566; J. Sprinz and G. Helmchen, Tetrahedron Lett, 1993, 34, 1769; G. J. Dawson, C. G. Frost, J. M. J. Williams, and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149; J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1994, 2065; J. M. Brown, D. I. Hulmes, and P. J. Guiry, Tetrahedron, 1994, 50, 4493; For a mechanistic study, see: J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, and L. Zsolnai, Tetrahedron Lett., 1994, 35, 1523.
5. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566; J. Sprinz and G. Helmchen, Tetrahedron Lett, 1993, 34, 1769; G. J. Dawson, C. G. Frost, J. M. J. Williams, and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149; J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1994, 2065; J. M. Brown, D. I. Hulmes, and P. J. Guiry, Tetrahedron, 1994, 50, 4493; For a mechanistic study, see: J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, and L. Zsolnai, Tetrahedron Lett., 1994, 35, 1523.
6. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566; J. Sprinz and G. Helmchen, Tetrahedron Lett, 1993, 34, 1769; G. J. Dawson, C. G. Frost, J. M. J. Williams, and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149; J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1994, 2065; J. M. Brown, D. I. Hulmes, and P. J. Guiry, Tetrahedron, 1994, 50, 4493; For a mechanistic study, see: J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, and L. Zsolnai, Tetrahedron Lett., 1994, 35, 1523.
7. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566; J. Sprinz and G. Helmchen, Tetrahedron Lett, 1993, 34, 1769; G. J. Dawson, C. G. Frost, J. M. J. Williams, and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149; J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1994, 2065; J. M. Brown, D. I. Hulmes, and P. J. Guiry, Tetrahedron, 1994, 50, 4493; For a mechanistic study, see: J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, and L. Zsolnai, Tetrahedron Lett., 1994, 35, 1523.
8. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566; J. Sprinz and G. Helmchen, Tetrahedron Lett, 1993, 34, 1769; G. J. Dawson, C. G. Frost, J. M. J. Williams, and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149; J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin, and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1994, 2065; J. M. Brown, D. I. Hulmes, and P. J. Guiry, Tetrahedron, 1994, 50, 4493; For a mechanistic study, see: J. Sprinz, M. Kiefer, G. Helmchen, M. Reggelin, G. Huttner, O. Walter, and L. Zsolnai, Tetrahedron Lett., 1994, 35, 1523.
9. J. M. Brown, D. I. Hulmes, and T. P. Layzell, J. Chem. Soc., Chem. Commun., 1993, 1673.
10. H. Kubota and K. Koga, Tetrahedron Lett., 1994, 35, 6689; H. Kubota, M. Nakajima, and K. Koga, Tetrahedron Lett., 1993, 34, 8135.
11. H. Kubota and K. Koga, Tetrahedron Lett., 1994, 35, 6689; H. Kubota, M. Nakajima, and K. Koga, Tetrahedron Lett., 1993, 34, 8135.
12. During the preparation of this manuscript, a paper was published which describes the synthesis of 3 and its use in asymmetric catalysis including allylic alkylation of 1,3-diphenyl-2-propenyl acetate with sodium dimethyl malonate: P. Wimmer and M. Widhalm, Tetrahedron: Asymmetry, 1995, 6, 657.
13. 3) δ: 54.05, 58.23 (d, J=15.9 Hz), 125-145 (ArC).
14. T. Hayashi, A. Yamamoto, Y. Ito, E. Nishioka, H. Miura, and K. Yanagi, J. Am. Chem. Soc., 1989, 111, 6301; T. Hayashi, K. Kishi, A. Yamamoto, and Y. Ito, Tetrahedron Lett., 1990, 31, 1743; B. M. Trost and D. L. Van Vranken, Angew. Chem., Int. Ed. Engl., 1992, 31, 228; B. M. Trost, D. L. Van Vranken, and C. Bingel, J. Am. Chem. Soc., 1992, 114, 9327; P. von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht, and G. Helmchen, Tetrahedron: Asymmetry, 1994, 5, 573.
15. T. Hayashi, A. Yamamoto, Y. Ito, E. Nishioka, H. Miura, and K. Yanagi, J. Am. Chem. Soc., 1989, 111, 6301; T. Hayashi, K. Kishi, A. Yamamoto, and Y. Ito, Tetrahedron Lett., 1990, 31, 1743; B. M. Trost and D. L. Van Vranken, Angew. Chem., Int. Ed. Engl., 1992, 31, 228; B. M. Trost, D. L. Van Vranken, and C. Bingel, J. Am. Chem. Soc., 1992, 114, 9327; P. von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht, and G. Helmchen, Tetrahedron: Asymmetry, 1994, 5, 573.
16. T. Hayashi, A. Yamamoto, Y. Ito, E. Nishioka, H. Miura, and K. Yanagi, J. Am. Chem. Soc., 1989, 111, 6301; T. Hayashi, K. Kishi, A. Yamamoto, and Y. Ito, Tetrahedron Lett., 1990, 31, 1743; B. M. Trost and D. L. Van Vranken, Angew. Chem., Int. Ed. Engl., 1992, 31, 228; B. M. Trost, D. L. Van Vranken, and C. Bingel, J. Am. Chem. Soc., 1992, 114, 9327; P. von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht, and G. Helmchen, Tetrahedron: Asymmetry, 1994, 5, 573.
17. T. Hayashi, A. Yamamoto, Y. Ito, E. Nishioka, H. Miura, and K. Yanagi, J. Am. Chem. Soc., 1989, 111, 6301; T. Hayashi, K. Kishi, A. Yamamoto, and Y. Ito, Tetrahedron Lett., 1990, 31, 1743; B. M. Trost and D. L. Van Vranken, Angew. Chem., Int. Ed. Engl., 1992, 31, 228; B. M. Trost, D. L. Van Vranken, and C. Bingel, J. Am. Chem. Soc., 1992, 114, 9327; P. von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht, and G. Helmchen, Tetrahedron: Asymmetry, 1994, 5, 573.
18. T. Hayashi, A. Yamamoto, Y. Ito, E. Nishioka, H. Miura, and K. Yanagi, J. Am. Chem. Soc., 1989, 111, 6301; T. Hayashi, K. Kishi, A. Yamamoto, and Y. Ito, Tetrahedron Lett., 1990, 31, 1743; B. M. Trost and D. L. Van Vranken, Angew. Chem., Int. Ed. Engl., 1992, 31, 228; B. M. Trost, D. L. Van Vranken, and C. Bingel, J. Am. Chem. Soc., 1992, 114, 9327; P. von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht, and G. Helmchen, Tetrahedron: Asymmetry, 1994, 5, 573.
19. B. M. Trost and E. Keinan, J. Org. Chem., 1979, 44, 3451.
20. 2 (9.1 mg, 0.025 mmol) in degassed THF (2.0 ml) was added chiral ligand (3) (34.2 mg, 0.06 mmol) under Ar atmosphere at room temperature. The pale yellow solution was degassed by freeze and thaw cycle and stirred for 30 min. The whole was treated successively with 1,3-diphenyl-2-propenyl acetate (252 mg, 1.0 mmol) in THF (3.0 ml) and benzylamine (214 mg, 2 mmol). The mixture was degassed and then stirred at 50°C for 2 h. After evaporation of the solvent, purification by silica gel chromatography (hexane-ether (6∼4:1)) afforded animation product as a colorless oil.