Catalytic Deprotection of Protected Alcohols in Water Using Low-Loading and Alkylated Polystyrene-Supported Sulfonic Acid

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8723-8725

  Iimura, Shinya ^a   Manabe, Kei ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC DEPROTECTION;

ALKYLATION; ETHERS; HYDROPHOBICITY; POLYSTYRENES; SOLVENTS;

ALCOHOLS;

ALCOHOL; ALKYL GROUP; BENZILIC ACID DERIVATIVE; ESTER; ETHER; POLYSTYRENE; SILANE DERIVATIVE; SOLVENT; SULFONIC ACID DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CATALYST SUPPORT; DEPROTECTION REACTION; HYDROPHOBICITY; REACTION ANALYSIS;

EID: 0142258935     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035178t     Document Type: Article

References (26)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999.
2. For a recent review of protecting groups, see: Jarowicki, K.; Kocienski, P. J. Chem. Soc., Perkin Trans. 1 2001, 2109.
3. (a) Trost, B. M. Science 1991, 254, 1471.
4. (b) Sheldon, R. A. Pure Appl. Chem. 2000, 72, 1233.
5. (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
6. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997.
7. For recent examples of polymer-supported catalysts which work in water, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567.
8. (b) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843.
9. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053.
10. (d) Chen, C.-W.; Chen, M.-Q.; Serizawa, T.; Akashi, M. Chem. Commun. 1998, 831.
11. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341.
12. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919.
13. (g) Tanaka, N.; Masaki, Y. Synlett 1999, 1960.
14. (h) Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
15. (i) Sakamoto, T.; Pac, C. J. Tetrahedron Lett. 2000, 41, 10009.
16. (j) Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837.
17. (a) Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2002, 344, 270.
18. (b) Iimura, S.; Manabe, K.; Kobayashi, S. Org. Lett. 2003, 5, 101.
19. (c) Iimura, S.; Nobutou, D.; Manabe, K.; Kobayashi, S. Chem. Commun. 2003, 1644.
20. Iimura, S.; Manabe, K.; Kobayashi, S. Org. Biomol. Chem. 2003, 1, 2416.
21. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
22. 3H.
23. For an excellent review of the selective deprotection of silyl ethers, see: Nelson, T. D.; Crouch, R. D. Synthesis 1996, 1031.
24. Suzuki, T.; Kobayashi, K.; Noda, K.; Oriyama, T. Synth. Commun. 2001, 31, 2761.
25. Recently, we have developed dehydration reactions such as esterification and etherification in water: (a) Manabe, K.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 10101.
26. (b) Manabe, K.; Iimura S.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 11971. See also ref 6a. For transprotection in water, see ref 6b.