Nucleophilic reactivities of silyl ketene acetals and silyl enol ethers containing (C6F5)3SiO and (C6H 5)3SiO groups

European Journal of Organic Chemistry

Volumn , Issue 9, 2005, Pages 1760-1764

  Dilman, Alexander D ^a   Mayr, Herbert ^b  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

Kinetics; Perfluorinated ligands; Silicon; Silyl ketene acetals and enol ethers; Substituent effects

Indexed keywords

EID: 18744376580     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400706     Document Type: Article

References (34)

1. a) T. Mukaiyama, Org. React. 1982, 28, 203-331;
2. b) E. M. Carreira, in: Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer-Verlag: Heidelberg) 1999, Vol. 3, pp. 997-1065;
3. C. Chuit, R. J. P. Corriu, C. Reye, J. Organomet. Chem. 1988, 358, 57-66;
4. R. Mahrwald, Chem. Rev. 1999, 99, 1095-1120.
5. a) D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480-4491;
6. b) M. Miyashita, T. Yanami, T. Kumazawa, A. Yoshikoshi, J. Am. Chem. Soc. 1984, 106, 2149-2156;
7. M. Santelli, J.-M. Pons, Lewis Acids and Selectivity in Organic Synthesis CRC Press, Boca Raton, 1996.
8. a) A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12964-12965;
9. b) S.-I. Murahashi, Y. Imada, T. Kawakami, K. Harada, Y. Yonemushi, N. Tomita, J. Am. Chem. Soc. 2002, 124, 2888-2889;
10. M. Sugiura, S. Kobayashi, Org. Lett. 2001, 3, 477-480;
11. M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096-1122;
12. Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
13. J. Burfeindt, M. Patz, M. Müller, H. Mayr, J. Am. Chem. Soc. 1998, 120, 3629-3634.
14. T. Tokuyasu, H. Mayr, Eur. J. Org. Chem. 2004, 2791-2796.
15. Alkyl vinyl ethers and dialkoxyalkenes are prone to polymerization in the presence of electrophilic reagents, see: a) P. R. Johnson, H. M. Barnes, S. M. McElvain, J. Am. Chem. Soc. 1940, 62, 964-972;
16. b) J. V. Crivello, Y.-L. Lai, R. Malik, J. Polym. Sci., Part A: Polym. Chem. 1996, 34, 3103-3120;
17. Z. Wu, L. Cao, C. U. Pittmann, Jr., J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 861-871;
18. Z. Wu, C. U. Pittmann, Jr., J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 873-881.
19. a) A. D. Dilman, P. A. Belyakov, A. A. Korlyukov, V. A. Tartakovsky, Tetrahedron Lett. 2004, 45, 3741-3744;
20. b) V. V. Levin, A. D. Dilman, P. A. Belyakov, A. A. Korlyukov, M. I. Struchkova, V. A. Tartakovsky, Eur. J. Org. Chem. 2004, 5141-5148.
21. a) H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77;
22. b) H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010;
23. Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957;
24. H. Mayr, M. Patz, M. F. Gotta, A. R. Ofial, Pure Appl. Chem. 1998, 70, 1993-2000.
25. H. Mayr, T. Bug, M. F. Gotta, N. Hering, B. Irrgang, B. Janker, B. Kempf, R. Loos, A. R. Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc. 2001, 123, 9500-9512.
26. R. Schneider, H. Mayr, P. H. Plesch, Ber. Bunsen-Ges. Phys. Chem. 1987, 91, 1369-1374.
27. H. Mayr, R. Schneider, C. Schade, J. Bartl, R. Bederke, J. Am. Chem. Soc. 1990, 112, 4446-4454.
28. p-Amino-substituted benzhydrylium ions are stable in trifluoroethanol, see: S. Minegishi, S. Kobayashi, H. Mayr, J. Am. Chem. Soc. 2004, 126, 5174-5181.
29. J. Bartl, S. Steenken, H. Mayr, J. Am. Chem. Soc. 1991, 113, 7710-7716.
30. According to Taft's constants the pentafluorophenyl group (σ* = 1.50) is a much stronger acceptor than phenyl (σ* = 0.60) and lies between 3,5-dinitrophenyl (σ* = 1.37) and difluoromethyl (σ* = 2.00) groups, see: T. Korenaga, K. Kadowaki, T. Ema, T. Sakai, J. Org. Chem. 2004, 69, 7340-7343.
31. Jpn. Kokai Tokkyo Koho, 1983, JP 58162585 (Chem. Abstr. 1984, 100:68153r). For 1b neither procedure nor spectroscopic data were reported.
32. a) M. Penso, D. Albanese, D. Landini, V. Lupi, J. Mol. Cat. A: Chem. 2003, 204-205, 177-185;
33. b) D. Albanese, D. Landini, M. Penso, S. Petricci, Synlett 1999, 199-200.
34. C. Jia, W. Lu, J. Oyamada, T. Kitamura, K. Matsuda, M. Irie, Y. Fujiwara, J. Am. Chem. Soc. 2000, 122, 7252-7263.