Chemoselective (trans)thioacetalization of carbonyl compounds with a reusable lewis acid-surfactant-combined copper bis(dodecyl sulfate) catalyst in water

Synthesis

Volumn , Issue 9, 2010, Pages 1493-1499

  Weng, Shiue Shien ^a   Chang, Shen Chun ^a   Chang, Tsuan Hao ^a   Chyn, Jong Pyng ^a   Lee, Shu Wei ^a   Lin, Chao An ^a   Chen, Fong Kuang ^a  

^a DEPARTMENT OF PHYSICS   (Taiwan)

Author keywords

Copper bis(dodecyl sulfate); Lewis acid surfactant combined catalysts; Reusability; Thioacetalization; Transthioacetalization

Indexed keywords

DODECYL SULFATE; LEWIS ACID-SURFACTANT-COMBINED CATALYST; THIOACETALIZATION; TRANSTHIOACETALIZATION;

CARBONYLATION; CATALYSTS; COPPER; ORGANIC SOLVENTS; REUSABILITY; SURFACE ACTIVE AGENTS;

METAL REFINING;

ACETAL DERIVATIVE; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; COPPER BIS(DODECYL SULFATE); KETONE DERIVATIVE; LEWIS ACID; ORGANIC SOLVENT; SURFACTANT; UNCLASSIFIED DRUG;

ACETALIZATION; ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; PURIFICATION; ROOM TEMPERATURE; STEREOCHEMISTRY; THIOACETALIZATION; TRANSTHIOACETALIZATION;

EID: 77955364959     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218693     Document Type: Article

References (64)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley & Sons: New York, 1999, 329.
2. (a) Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1075.
3. (b) Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231.
4. (c) Grobel, B. T.; Seebach, D. Synthesis 1977, 357.
5. (d) Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
6. (e) Smith, A. B. III; Christopher, M. A. Acc. Chem. Res. 2004, 37, 365.
7. (a) Yus, M.; Nájera, C.; Foubelo, F. Tetrahedron 2003, 59, 6147.
8. (b) Smith, A. B. III; Pitram, S. M.; Gaunt, M. J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 14516.
9. (c) Takeda, T.; Kuroi, S.; Yanai, K.; Tsubouchi, A. Tetrahedron Lett. 2002, 43, 5641.
10. (d) Smith, A. B. III; Lin, Q.; Doughty, V. A.; Zhuang, L.; McBriar, M. D.; Kerns, J. K.; Brook, C. S.; Murase, N.; Nakayama, K. Angew. Chem. Int. Ed. 2001, 40, 196.
11. (e) Breit, B. Angew. Chem. Int. Ed. 1998, 37, 453.
12. (f) Horikawa, Y.; Watanabe, M.; Fujiwara, T.; Takeda, T. J. Am. Chem. Soc. 1997, 119, 1127.
13. Truce, W. E.; Roberts, F. E. J. Org. Chem. 1963, 28, 961.
14. Garlaschelli, L.; Vidari, G. Tetrahedron Lett. 1990, 31, 5815.
15. Patney, H. K. Tetrahedron Lett. 1991, 32, 2259.
16. (a) Khan, A. T.; Parvin, T.; Choudhury, L. H. Synthesis 2006, 2497.
17. (b) Kamitori, T.; Hojo, K.; Masuda, R.; Kimura, T.; Yoshida, T. J. Org. Chem. 1986, 51, 1427.
18. (a) Patney, H. K.; Margan, S. Tetrahedron Lett. 1996, 37, 4621.
19. (b) Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1999, 319.
20. Anand, R.; Saravanan, V. P.; Singh, V. K. Synlett 1999, 415.
21. Ong, B. S. Tetrahedron Lett. 1980, 21, 4225.
22. Tani, H.; Masumoto, K.; Inamasu, T. Tetrahedron Lett. 1991, 32, 2039.
23. Das, N. B.; Nayak, A.; Sharma, R. P. J. Chem. Res., Synop. 1993, 242.
24. Ku, B.; Oh, D. Y. Synth. Commun. 1989, 19, 433.
25. Kumar, V.; Dev, S. Tetrahedron Lett. 1983, 24, 1289.
26. (a) Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2001, 42, 359.
27. (b) Muthusamy, S.; Babu, S. A.; Gunanathan, C. Synth. Commun. 2001, 31, 1205.
28. Fieser, L. F. J. Am. Chem. Soc. 1954, 76, 1945.
29. Corey, E. J.; Shimoji, K. Tetrahedron Lett. 1983, 24, 169.
30. (a) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527.
31. (b) Deka, N.; Sarma, J. C. Chem. Lett. 2001, 749; and references cited therein.
32. Perni, R. B. Synth. Commun. 1989, 19, 2383.
33. Saraswathy, V. G.; Sankararaman, S. J. Org. Chem. 1994, 59, 4665.
34. De S, K. Synthesis 2004, 2837.
35. De S, K. Tetrahedron Lett. 2004, 45, 1035.
36. Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1998, 739.
37. Kazahaya, K.; Tsuneo, S.; Sato, T. Synlett 2004, 1640.
38. Kamal, A.; Chouhan, G. Synlett 2002, 474.
39. (a) Kamal, A.; Chouhan, G. Tetrahedron Lett. 2002, 43, 1347.
40. (b) Kamal, A.; Chouhan, G. Tetrahedron Lett. 2003, 44, 3337.
41. (c) De S, K. Synthesis 2004, 828.
42. De S, K. J. Mol. Catal. A: Chem. 2005, 232, 77.
43. (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998.
44. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley & Sons: New York, 1997.
45. (c) Breslow, R. Acc. Chem. Res. 1991, 24, 159.
46. (a) Manabe, K.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 10101.
47. (b) Manabe, K.; Iimura, S.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 11971.
48. (c) Mori, Y.; Manabe, K.; Kobayashi, S. Angew. Chem. Int. Ed. 2001, 40, 2815.
49. (d) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209; and references cited therein.
50. (a) Otto, S.; Engberts, J. B. F. N.; Kwak, J. C. T. J. Am. Chem. Soc. 1998, 120, 9517.
51. (b) Otto, S.; Engberts, J. B. F. N.; Kwak, J. C. T. J. Am. Chem. Soc. 1999, 121, 6798.
52. (a) Kobayashi, S.; Mori, Y.; Nagayama, S.; Manabe, K. Green Chem. 1999, 1, 175.
53. (b) Manabe, K.; Mori, Y.; Kobayashi, S. Synlett 1999, 1401.
54. (c) Manabe, K.; Kobayashi, S. Org. Lett. 1999, 1, 1965.
55. (d) Manabe, K.; Mori, Y.; Kobayashi, S. Tetrahedron 2001, 57, 2537.
56. (e) Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1426.
57. Ceschi, M.; Felix, A. L. D. A.; Peppe, C. Tetrahedron Lett. 2000, 41, 9695.
58. (a) Moroi, Y.; Motomura, K.; Matuura, R. J. Colloid Interface Sci. 1974, 46, 111.
59. (b) Kamenka, N.; Burgaud, I.; Treiner, C.; Zana, R. Langmuir 1994, 10, 3455.
60. (a) Satake, I.; Iwamatsu, I.; Hosokawa, S.; Matuura, R. Bull. Chem. Soc. Jpn. 1963, 36, 204.
61. (b) Satake, I.; Matuura, R. Bull. Chem. Soc. Jpn. 1963, 36, 813.
62. Several catalytic transthioacetalization systems are faster and more efficient than direct thioacetalization; see: (a) Muthusamy, A.; Babu, S. A.; Gunanathan, C. Tetrahedron 2002, 58, 7897.
63. (b) Ranu, B. C.; Das, A.; Samanta, S. Synlett 2002, 727.
64. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1993, 58, 4971.