Simple, mild and efficient thioacetalization and transthioacetalization of carbonyl compounds and deprotection of thioacetals: Unique role of thiols in the selectivity of thioacetalization

Synthesis

Volumn , Issue 2, 2005, Pages 250-254

  Das, Biswanath ^a   Ramu, Ravirala ^a   Reddy, Majjigapu Ravinder ^a   Mahender, Gurram ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Carbonyl compounds; Deprotection of thioacetals; NaHSO4 SiO2; Selectivity; Thioacetalization; Transthioacetalization

Indexed keywords

CATALYST SELECTIVITY; HYDROGEN INORGANIC COMPOUNDS; REACTION KINETICS; SILICA; THERMAL EFFECTS;

HYDROGEN SULFATE; ROOM TEMPERATURE (RT); THIOACETALIZATION; TRANSTHIOACETALIZATION;

SYNTHESIS (CHEMICAL);

ACETAL; CARBONYL DERIVATIVE; HYDROGEN; METHYL CHLORIDE; SILICON DIOXIDE; SODIUM; SODIUM HYDROGEN SULFATE; SULFATE; THIOACETAL; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ACETALIZATION; ARTICLE; CATALYST; CATALYST SUPPORT; DEPROTECTION REACTION; REACTION ANALYSIS; ROOM TEMPERATURE; THIOACETALIZATION; TRANSTHIOACETALIZATION;

EID: 13844270645     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834934     Document Type: Article

References (26)

1. Part 39 in the series 'Studies on novel synthetic methodologies'; IICT Communication No. 041106.
2. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991, 178-207.
3. (b) Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994, 156-170.
4. (a) Corey, E. J.; Seebach, D. Angew Chem. Int. Ed. Engl. 1965, 4, 1075.
5. (b) Corey, E. J.; Seebach, D. J. Org. Chem. 1966, 31, 4097.
6. (a) Colvin, E. W.; Raphael, R. A.; Roberts, J. S. J. Chem. Soc., Chem. Commun. 1971, 858.
7. (b) Corey, E. J.; Erickson, B. W. J. Org. Chem. 1971, 36, 3553.
8. (c) Ho, T. L.; Ho, H. C.; Wong, C. M. J. Chem. Soc., Chem. Commun. 1972, 791.
9. (d) Dishi, T.; Kamemoto, K.; Ban, Y. Tetrahedron Lett. 1972, 13, 1085.
10. (e) Ellision, R. A.; Lukenbach, E. R.; Chiu, C. W. Tetrahedron Lett. 1975, 499.
11. (f) Schmittel, M.; Levis, M. Synlett 1996, 315.
12. (g) Hirano, A.; Ukawar, K.; Yakabe, S.; Clark, J. H.; Morimoto, T. Synthesis 1997, 858.
13. (a) Dijerassi, C.; Gorman, M. J. Am. Chem. Soc. 1953, 75, 3704.
14. (b) Fieser, L. F. J. Am. Chem. Soc. 1954, 76, 1945.
15. (c) Olah, G. A.; Narang, S. C.; Meider, D.; Salem, G. F. Synthesis 1981, 282.
16. (d) Corey, E. J.; Shimoji, K. Tetrahedron Lett. 1983, 24, 169.
17. (e) Page, P. C. B.; Prodger, J. C.; Westwood, D. Tetrahedron 1993, 49, 10355.
18. (f) Tateiwa, J.; Horiuchi, H.; Uemura, S. J. Org. Chem. 1995, 60, 4039.
19. (g) Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synthesis 1999, 58.
20. (h) Yadav, J. S.; Reddy, B. V. S.; Pandey, S. K. Synlett 2001, 238.
21. (i) Kamal, A.; Choudhan, G. Tetrahedron Lett. 2003, 44, 3337.
22. (j) Yadav, J. S.; Reddy, B. V. S.; Kondaji, G. Chem. Lett. 2003, 32, 672.
23. (a) Mahender, G.; Ramu, R.; Ramesh, C.; Das, B. Chem. Lett. 2003, 32, 734.
24. (b) Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Adv. Synth. Catal. 2003, 557.
25. (c) Ramesh, C.; Ravindranath, N.; Das, B. J. Org. Chem. 2003, 68, 7101.
26. Breton, G. W. J. Org. Chem. 1997, 62, 8952.