α,α-diacetyl cyclic ketene dithioacetals: Odorless and efficient dithiol equivalents in thioacetalization reactions

Synlett

Volumn , Issue 6, 2004, Pages 999-1002

  Yu, Haifeng ^a   Liu, Qun ^a   Yin, Yanbing ^a   Fang, Qunxin ^a   Zhang, Jingping ^a   Dong, Dewen ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

Aldehyde; Ketone; Thioacetalization; Thiol; , diacetyl cyclic ketene dithioacetal

Indexed keywords

ACETAL DERIVATIVE; DITHIOL DERIVATIVE;

ACETALIZATION; ARTICLE; ODOR;

EID: 3142746647     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822892     Document Type: Article

References (30)

1. (a) Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994.
2. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons: New York, 1999.
3. (a) Breit, B. Angew. Chem. Int. Ed. 1998, 37, 453.
4. (b) Smith, A. B. III; Pitram, S. M.; Gaunt, M. J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 14516.
5. (a) Ku, B.; Oh, D. Y. Synth. Commun. 1989, 19, 433.
6. (b) Page, P. C. B.; Prodger, J. C.; Westwood, D. Tetrahedron 1993, 49, 10355.
7. (c) Tani, H.; Masumoto, K.; Inamasu, T.; Suzuki, H. Tetrahedron Lett. 1991, 32, 2039.
8. (d) Tietze, L. F.; Weigand, B.; Wulff, C. Synthesis 2000, 69.
9. (a) Garlaschelli, L.; Vidari, G. Tetrahedron Lett. 1990, 31, 5815.
10. (b) Patney, H. K. Tetrahedron Lett. 1991, 32, 2259.
11. (c) Kumar, P.; Reddy, R. S.; Singh, A. P.; Pandey, B. Tetrahedron Lett. 1992, 33, 825.
12. (d) Saraswathy, V. G.; Sankararaman, S. J. Org. Chem. 1994, 59, 4665.
13. (e) Anand, R. V.; Saravanan, P.; Singh, V. K. Synlett 1999, 415.
14. (f) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527.
15. (g) Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2001, 42, 359.
16. (h) Samajdar, S.; Basu, M. K.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2001, 42, 4425.
17. (i) Kamal, A.; Chouhan, G. Tetrahedron Lett. 2002, 43, 1347.
18. (j) Firouzabadi, H.; Iranpoor, N.; Amani, K. Synthesis 2002, 59.
19. (k) Kamal, A.; Chouhan, G. Tetrahedron Lett. 2003, 44, 3337.
20. (a) Node, M.; Kumura, K.; Nishide, K.; Ohsugi, S.; Miyamoto, T. Tetrahedron Lett. 2001, 42, 9207.
21. (b) Nishide, K.; Miyamoto, T.; Kumura, K.; Ohsugi, S. I.; Node, M. Tetrahedron Lett. 2002, 43, 8569.
22. (c) Nishide, K.; Ohsugi, S. I.; Fudesaka, M.; Kodama, S.; Node, M. Tetrahedron Lett. 2002, 43, 5177.
23. (a) Bertini, V.; Lucchesini, F.; Pocci, M.; De Munno, A. Tetrahedron Lett. 1998, 39, 9263.
24. (b) Bertini, V.; Lucchesini, F.; Pocci, M.; De Munno, A. J. Org. Chem. 2000, 65, 4839.
25. (c) Bertini, V.; Pocci, M.; Lucchesini, F.; Alfei, S.; De Munno, A. Synlett 2003, 864.
26. Limura, S.; Manabe, K.; Kobayashi, S. Org. Lett. 2003, 5, 101.
27. Liu, Q.; Che, G.; Yu, H.; Liu, Y.; Zhang, J.; Zhang, Q.; Dong, D. J. Org. Chem. 2003, 68, 9148.
28. (a) Choi, E. B.; Youn, I. K.; Pak, C. S Synthesis 1988, 792.
29. (b) Mellor, J. M.; Schofield, S. R.; Korn, S. R. Tetrahedron 1997, 55, 17151.
30. 1H NMR, IR spectroscopy and elemental analyses, the data for these compounds are in good agreement with that in literatures.