Asymmetric protonation of silyl enolates catalyzed by chiral phosphine-silver(I) complexes

Pure and Applied Chemistry

Volumn 78, Issue 2, 2006, Pages 519-523

  Yanagisawa, Akira ^a   Touge, Taichiro ^a   Arai, Takayoshi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Alcohol; Asymmetric catalysis; Protonation; Silver; Silyl enolate

Indexed keywords

EID: 33644500110     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200678020519     Document Type: Conference Paper

References (32)

1. Reviews: (a) S. Hünig. In Houben-Weyl: Methods of Organic Chemistry, Vol. E 21, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann (Eds.), p. 3851, Georg Thieme Verlag, Stuttgart (1995);
2. (b) C. Fehr. Angew. Chem., Int. Ed. Engl. 35, 2566 (1996);
3. (c) A. Yanagisawa and H. Yamamoto. In Comprehensive Asymmetric Catalysis III, E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), p. 1295, Springer, Heidelberg (1999);
4. (d) J. Eames and N. Weerasooriya. Tetrahedron: Asymmetry 12, 1 (2001);
5. (e) P. I. Dalko and L. Moisan. Angew. Chem., Int. Ed. 40, 3726 (2001);
6. (f) A. Yanagisawa. In Comprehensive Asymmetric Catalysis, Supplement 2, E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), p. 125, Springer, Heidelberg (2004);
7. (g) L. Duhamel, P. Duhamel, J.-C. Plaquevent. Tetrahedron: Asymmetry 15, 3653 (2004).
8. For notable recent examples of asymmetric protonation: (a) K. Ishihara, D. Nakashima, Y. Hiraiwa, H. Yamamoto. J. Am. Chem. Soc. 125, 24 (2003);
9. (b) Y. Ohtsuka, T. Ikeno, T. Yamada. Tetrahedron: Asymmetry 14, 967 (2003);
10. (c) G. Asensio, A. Cuenca, N. Rodriguez, M. Medio-Simón. Tetrahedron: Asymmetry 14, 3851 (2003);
11. (d) L. Navarre, S. Darses, J.-P. Genet. Angew. Chem., Int. Ed. 43, 719 (2004);
12. (e) D. R. Carbery and T. J. Donohoe. Chem. Commun. 722 (2004);
13. (f) B. M. Kim, H. Kim, W. Kim, K. Y. Im, J. K. Park. J. Org. Chem. 69, 5104 (2004);
14. (g) Y. Hamashima, H. Somei, Y. Shimura, T. Tamura, M. Sodeoka. Org. Lett. 6, 1861 (2004);
15. (h) G. Liang and D. Trauner. J. Am. Chem. Soc. 126, 9544 (2004);
16. (i) R. J. Moss, K. J. Wadsworth, C. J. Chapman, C. G. Frost. Chem. Commun. 1984 (2004);
17. (j) T. J. Donohoe, G. C. Freestone, C. E. Headley, C. L. Rigby, R. P. C. Cousins, G. Bhalay. Org. Lett. 6, 3055 (2004);
18. (k) E. Boyd, G. S. Coumbarides, J. Eames, A. Hay, R. V. H. Jones, R. A. Stenson, M. J. Suggate. Tetrahedron Lett. 45, 9465 (2004);
19. (l) G. S. Coumbarides, J. Eames, S. Ghilagaber, M. J. Suggate. Tetrahedron Lett. 45, 9469 (2004);
20. (m) G. S. Coumbarides, J. Eames, J. E. W. Scheuermann, K. F. Sibbons, M. J. Suggate, M. Watkinson. Bull. Chem. Soc. Jpn. 78, 906 (2005);
21. (n) S. L. Wiskur and G. C. Fu. J. Am. Chem. Soc. 127, 6176 (2005);
22. (o) M. P. Sibi, H. Tatamidani, K. Paul. Org. Lett. 7, 2571 (2005);
23. (p) C. Schaefer and G. C. Fu. Angew. Chem., Int. Ed. 44, 4606 (2005);
24. (q) D. Nakashima and H. Yamamoto. Synlett 150 (2006).
25. A. Yanagisawa, T. Watanabe, T. Kikuchi, H. Yamamoto. J. Org. Chem. 65, 2979 (2000).
26. (a) K. Ishihara, S. Nakamura, M. Kaneeda, H. Yamamoto. J. Am. Chem. Soc. 118, 12854 (1996);
27. (b) S. Nakamura, M. Kaneeda, K. Ishihara, H. Yamamoto. J. Am. Chem. Soc. 122, 8120 (2000); Nakai et al. reported a chiral cationic Pd complex-catalyzed asymmetric protonation of silyl enolates by water;
28. (c) M. Sugiura and T. Nakai. Angew. Chem., Int. Ed. Engl. 36, 2366 (1997).
29. A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y. Matsumoto, H. Yamamoto. Angew. Chem., Int. Ed. 38, 3701 (1999).
30. (a) A. Yanagisawa, Y. Nakatsuka, K. Asakawa, H. Kageyama, H. Yamamoto. Synlett 69 (2001);
31. (b) A. Yanagisawa, Y. Nakatsuka, K. Asakawa, M. Wadamoto, H. Kageyama, H. Yamamoto. Bull. Chem. Soc. Jpn. 74, 1477 (2001).
32. A. Yanagisawa, T. Touge, T. Arai. Angew. Chem., Int. Ed. 44, 1546 (2005).