Scandium Trifluoromethanesulfonimide and Scandium Trifluoromethanesulfonate as Extremely Active Acetalization Catalysts

Synlett

Volumn 1996, Issue 9, 1996, Pages 839-841

  Ishihara, Kazuaki ^a   Karumi, Yoshinori ^a   Kubota, Manabu ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000773319     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5594     Document Type: Article

References (22)

1. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons, Inc.: New York; 1991; 2nd Ed.
2. (b) Meskens, F. A. J. Synthesis 1981, 501.
3. Seebach, D.; Imwinkelried, R.; Weber, T. Modern Synthetic Methods 1986, Scheffold, R., Ed.; Springer Verlag: Berlin, Heidelberg, 1986; vol. 4, pp 125-259.
4. For the preparation of acetals using Lewis acid catalysts, see: (a) Alper, H.; Dinkes, L. Synthesis 1972, 81. (b) Noyori, R.; Tsunoda, T.; Suzuki, M. Tetrahedron Lett. 1980, 21, 1357. (c) Ott, J.; Ramos Tombo, G. M.; Schmid, B.; Venanzi, L. M.; Wang, G.; Ward, T. R. Tetrahedron Lett. 1989, 30, 6151. (d) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690 and references cited therein. (e) Ma, S.; Venanzi, L. M. Tetrahedron Lett. 1993, 34, 5269. (f) Fukuzawa, S.; Tsuchimoto, T.; Hotaka, T.; Hiyama, T. Synlett 1995, 1077.
5. For the preparation of acetals using Lewis acid catalysts, see: (a) Alper, H.; Dinkes, L. Synthesis 1972, 81. (b) Noyori, R.; Tsunoda, T.; Suzuki, M. Tetrahedron Lett. 1980, 21, 1357. (c) Ott, J.; Ramos Tombo, G. M.; Schmid, B.; Venanzi, L. M.; Wang, G.; Ward, T. R. Tetrahedron Lett. 1989, 30, 6151. (d) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690 and references cited therein. (e) Ma, S.; Venanzi, L. M. Tetrahedron Lett. 1993, 34, 5269. (f) Fukuzawa, S.; Tsuchimoto, T.; Hotaka, T.; Hiyama, T. Synlett 1995, 1077.
6. For the preparation of acetals using Lewis acid catalysts, see: (a) Alper, H.; Dinkes, L. Synthesis 1972, 81. (b) Noyori, R.; Tsunoda, T.; Suzuki, M. Tetrahedron Lett. 1980, 21, 1357. (c) Ott, J.; Ramos Tombo, G. M.; Schmid, B.; Venanzi, L. M.; Wang, G.; Ward, T. R. Tetrahedron Lett. 1989, 30, 6151. (d) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690 and references cited therein. (e) Ma, S.; Venanzi, L. M. Tetrahedron Lett. 1993, 34, 5269. (f) Fukuzawa, S.; Tsuchimoto, T.; Hotaka, T.; Hiyama, T. Synlett 1995, 1077.
7. For the preparation of acetals using Lewis acid catalysts, see: (a) Alper, H.; Dinkes, L. Synthesis 1972, 81. (b) Noyori, R.; Tsunoda, T.; Suzuki, M. Tetrahedron Lett. 1980, 21, 1357. (c) Ott, J.; Ramos Tombo, G. M.; Schmid, B.; Venanzi, L. M.; Wang, G.; Ward, T. R. Tetrahedron Lett. 1989, 30, 6151. (d) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690 and references cited therein. (e) Ma, S.; Venanzi, L. M. Tetrahedron Lett. 1993, 34, 5269. (f) Fukuzawa, S.; Tsuchimoto, T.; Hotaka, T.; Hiyama, T. Synlett 1995, 1077.
8. For the preparation of acetals using Lewis acid catalysts, see: (a) Alper, H.; Dinkes, L. Synthesis 1972, 81. (b) Noyori, R.; Tsunoda, T.; Suzuki, M. Tetrahedron Lett. 1980, 21, 1357. (c) Ott, J.; Ramos Tombo, G. M.; Schmid, B.; Venanzi, L. M.; Wang, G.; Ward, T. R. Tetrahedron Lett. 1989, 30, 6151. (d) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690 and references cited therein. (e) Ma, S.; Venanzi, L. M. Tetrahedron Lett. 1993, 34, 5269. (f) Fukuzawa, S.; Tsuchimoto, T.; Hotaka, T.; Hiyama, T. Synlett 1995, 1077.
9. For the preparation of acetals using Lewis acid catalysts, see: (a) Alper, H.; Dinkes, L. Synthesis 1972, 81. (b) Noyori, R.; Tsunoda, T.; Suzuki, M. Tetrahedron Lett. 1980, 21, 1357. (c) Ott, J.; Ramos Tombo, G. M.; Schmid, B.; Venanzi, L. M.; Wang, G.; Ward, T. R. Tetrahedron Lett. 1989, 30, 6151. (d) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690 and references cited therein. (e) Ma, S.; Venanzi, L. M. Tetrahedron Lett. 1993, 34, 5269. (f) Fukuzawa, S.; Tsuchimoto, T.; Hotaka, T.; Hiyama, T. Synlett 1995, 1077.
10. For the preparation of dioxolanones and dioxanones using Lewis acid catalysts, see: (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 26, 2945. (c) Seebach, D.; Zimmerman, J. Helv. Chim. Acta 1986, 69, 1147. (d) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448. (e) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351. (f) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353. (g) References 3c and 3d. (h) Chapel, N.; Greiner, A.; Ortholand, J-Y. Tetrahedron Lett. 1991, 32, 1441. (i) Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1880.
11. For the preparation of dioxolanones and dioxanones using Lewis acid catalysts, see: (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 26, 2945. (c) Seebach, D.; Zimmerman, J. Helv. Chim. Acta 1986, 69, 1147. (d) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448. (e) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351. (f) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353. (g) References 3c and 3d. (h) Chapel, N.; Greiner, A.; Ortholand, J-Y. Tetrahedron Lett. 1991, 32, 1441. (i) Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1880.
12. For the preparation of dioxolanones and dioxanones using Lewis acid catalysts, see: (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 26, 2945. (c) Seebach, D.; Zimmerman, J. Helv. Chim. Acta 1986, 69, 1147. (d) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448. (e) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351. (f) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353. (g) References 3c and 3d. (h) Chapel, N.; Greiner, A.; Ortholand, J-Y. Tetrahedron Lett. 1991, 32, 1441. (i) Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1880.
13. For the preparation of dioxolanones and dioxanones using Lewis acid catalysts, see: (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 26, 2945. (c) Seebach, D.; Zimmerman, J. Helv. Chim. Acta 1986, 69, 1147. (d) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448. (e) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351. (f) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353. (g) References 3c and 3d. (h) Chapel, N.; Greiner, A.; Ortholand, J-Y. Tetrahedron Lett. 1991, 32, 1441. (i) Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1880.
14. For the preparation of dioxolanones and dioxanones using Lewis acid catalysts, see: (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 26, 2945. (c) Seebach, D.; Zimmerman, J. Helv. Chim. Acta 1986, 69, 1147. (d) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448. (e) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351. (f) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353. (g) References 3c and 3d. (h) Chapel, N.; Greiner, A.; Ortholand, J-Y. Tetrahedron Lett. 1991, 32, 1441. (i) Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1880.
15. For the preparation of dioxolanones and dioxanones using Lewis acid catalysts, see: (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 26, 2945. (c) Seebach, D.; Zimmerman, J. Helv. Chim. Acta 1986, 69, 1147. (d) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448. (e) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351. (f) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353. (g) References 3c and 3d. (h) Chapel, N.; Greiner, A.; Ortholand, J-Y. Tetrahedron Lett. 1991, 32, 1441. (i) Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1880.
16. For the preparation of dioxolanones and dioxanones using Lewis acid catalysts, see: (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 26, 2945. (c) Seebach, D.; Zimmerman, J. Helv. Chim. Acta 1986, 69, 1147. (d) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448. (e) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351. (f) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353. (g) References 3c and 3d. (h) Chapel, N.; Greiner, A.; Ortholand, J-Y. Tetrahedron Lett. 1991, 32, 1441. (i) Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1880.
17. For the preparation of dioxolanones and dioxanones using Lewis acid catalysts, see: (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 26, 2945. (c) Seebach, D.; Zimmerman, J. Helv. Chim. Acta 1986, 69, 1147. (d) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448. (e) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351. (f) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353. (g) References 3c and 3d. (h) Chapel, N.; Greiner, A.; Ortholand, J-Y. Tetrahedron Lett. 1991, 32, 1441. (i) Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1880.
18. For the preparation of dioxolanones and dioxanones using Lewis acid catalysts, see: (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 26, 2945. (c) Seebach, D.; Zimmerman, J. Helv. Chim. Acta 1986, 69, 1147. (d) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448. (e) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351. (f) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 1353. (g) References 3c and 3d. (h) Chapel, N.; Greiner, A.; Ortholand, J-Y. Tetrahedron Lett. 1991, 32, 1441. (i) Ortholand, J.-Y.; Vicart, N.; Greiner, A. J. Org. Chem. 1995, 60, 1880.
19. (a) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413, 6639 (corrections).
20. (b) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265.
21. (c) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, in press.
22. In the acylation of alcohols with carboxylic acid anhydrides catalyzed by scandium complexes, acetonitrile is the most suitable solvent.