Scandium(III) Triflate as an Efficient and Recyclable Catalyst for Chemoselective Conversion of Carbonyl Compounds to 1,3-Oxathiolanes

Synthesis

Volumn , Issue 16, 2003, Pages 2503-2506

  Karimi, Babak ^a   Ma'mani, Leila ^a  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

Author keywords

Acetals; Aldehydes; Catalysis; Heterocycles; Ketones; Protecting groups; Scandium

Indexed keywords

ALDEHYDES; CATALYSTS; KETONES; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVITY;

SCANDIUM COMPOUNDS;

1,3 OXATHIOLANE DERIVATIVE; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; CHLORIDE; KETONE DERIVATIVE; SCANDIUM; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; METHODOLOGY; PRODUCT RECOVERY; RECYCLING; SYNTHESIS;

EID: 0344010962     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42436     Document Type: Article

References (32)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999, Chap. 4.
2. (a) Fuji, K.; Ueda, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1977, 814.
3. (b) Fuji, K.; Ueda, M.; Sumi, K.; Kajiwara, K.; Fujita, E.; Iwashita, T. ; Miura, I. J. Org. Chem. 1985, 50, 657.
4. (c) Fuji, K.; Ueda, M.; Sumi, K.; Fujita, E. Tetrahedron Lett. 1981, 22, 2005.
5. (d) Fuji, K.; Ueda, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1983, 49.
6. (a) Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943.
7. (b) Eliel, E. L.; Morris-Natschke, S. J. Am. Chem. Soc. 1984, 106, 2937.
8. (c) Frye, S. V.; Eliel, E. L. Tetrahedron Lett. 1985, 26, 3907.
9. (d) Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 21, 2859.
10. (a) Isobe, M.; Obeyama, J.; Funabashi, Y.; Goto, T. Tetrahedron Lett. 1988, 29, 4773.
11. (b) Utimoto, K.; Nakamura, A.; Matsubara, S. J. Am. Chem. Soc. 1990, 112, 8189.
12. Ralls, J. W.; Dodson, R. M.; Riegel, B. J. Am. Chem. Soc. 1949, 71, 3320.
13. Mondal, E.; Sahu, P. R.; Khan, A. T. Synlett 2002, 463.
14. Djerssi, C.; Gorman, M. J. Am. Chem. Soc. 1953, 75, 3704.
15. Wilson, G. E. Jr.; Huang, M. G.; Schloman, W. W. Jr. J. Org. Chem. 1968, 33, 2133.
16. Mondal, E.; Sahu, P. R.; Bose, G.; Khan, A. T. Tetrahedron Lett. 2002, 43, 2843.
17. Ravindranathan, T.; Chavan, S. P.; Dantale, W. Tetrahedron Lett. 1995, 36, 2285.
18. Streinz, L.; Koutek, B.; Saman, D. Coll. Czech. Chem. Commun. 1997, 62, 665.
19. Burczyk, B.; Kortylewicz, Z. Synthesis 1982, 831.
20. Karimi, B.; Seradj, H. Synlett 2000, 805.
21. Romo, J.; Rosenkranz, G.; Djerassi, C. J. Am. Chem. Soc. 1951, 73, 4961.
22. (a) For a review, see: Kobayashi, S. Eur. J. Org. Chem. 1999, 1, 15. (b) See also: Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227.
23. (a) For a review, see: Kobayashi, S. Eur. J. Org. Chem. 1999, 1, 15. (b) See also: Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227.
24. Kobayashi, S. Synlett 1994, 689.
25. Crotti, P.; Bussol, V. D.; Favero, L.; Psero, M. J. Org. Chem. 1996, 61, 9548.
26. Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755.
27. Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545.
28. Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472.
29. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527.
30. Eliel, E. L. J. Am. Chem. Soc. 1959, 81, 6087.
31. Marshall, J. R.; Stevenson, H. A. J. Chem. Soc. 1959, 2360.
32. Eliel, E. L.; Pilate, L. A.; Badding, V. G. J. Am. Chem. Soc. 1962, 84, 2377.