Highly efficient deprotection of aromatic acetals under neutral conditions using β-cyclodextrin in water

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 2018-2019

  Srilakshmi Krishnaveni, N ^a   Surendra, K ^a   Arjun Reddy, M ^a   Nageswar, Y V D ^a   Rama Rao, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETIC CONDITIONS;

ALDEHYDES; BIOMIMETIC MATERIALS; WATER;

AROMATIC COMPOUNDS;

ACETAL DERIVATIVE; ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; BETA CYCLODEXTRIN; WATER;

ARTICLE; BIOMIMETICS; CATALYSIS; CATALYST; CHEMICAL REACTION; HYDROGEN BOND; REACTION ANALYSIS; TECHNIQUE;

ACETALS; CATALYSIS; CHEMISTRY, ORGANIC; CYCLODEXTRINS; INDICATORS AND REAGENTS; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 0037424441     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026482+     Document Type: Article

References (32)

1. Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis, 2nd ed.; Wilely & Sons: New York, 1991.
2. (a) Gros, P.; LePerchec, P.; Senet, J. P. J. Chem. Res., Synop. 1995, 196.
3. (b) Wu, S. H.; Ding, Z.-B. Synth. Commun. 1994, 24, 2173.
4. (c) Ma, S.; Venanzi, L. M. Tetrahedron Lett. 1993, 34, 8071.
5. (d) Chang, C.; Chu, K. C.; Yue, S. Synth. Commun. 1992, 22, 1217.
6. (e) Mandal, A. K.; Shrotri, P. Y.; Ghogare, A. D. Synthesis 1986, 221.
7. (f) Kim, K. S.; Song, Y. H.; Lee, B. H.; Hahn, C. S. J. Org. Chem. 1986, 51, 404.
8. (g) Lipshutz, B. H.; Pollart, D.; Monforte, J.; Kotsuki, H. Tetrahedron Lett. 1985, 26, 705.
9. (h) Lipshutz, B. H.; Harvey, D. F. Synth. Commun. 1982, 12, 267.
10. (i) Balme, G.; Gore, J. J. Org. Chem. 1983, 48, 3336.
11. (a) Johnstone, C.; Kerr, W. J.; Scott, J. S. Chem. Commun. 1996, 341.
12. (b) Denis, J. N.; Krief, A. Angew. Chem., Int. Ed. Engl. 1980, 19, 1006.
13. (a) Olah, G. A.; Husain, A.; Singh, B. P.; Mehrotra, A. K. J. Org. Chem. 1983, 48, 3667.
14. (b) Jung, M. E.; Andrus, W. A.; Ornstein, P. L. Tetrahedron Lett. 1977, 4175.
15. Gautier, E. C. L.; Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. J. K. Tetrahedron Lett. 1997, 38, 1881.
16. Trehan, A.; Vij, A.; Walia, M.; Kaur, G.; Verma, R. D.; Trehan, S. Tetrahedron Lett. 1993, 34, 7335.
17. Tanemura, K.; Suzuki, T.; Horaguchi, T. Chem. Commun. 1992, 979.
18. (a) Reddy, M. A.; Surendra, K.; Bhanumathi, N.; Rao, K. R. Tetrahedron 2002, 58, 6003.
19. (b) Reddy, M. A.; Bhanumathi, N.; Rao, K. R. Tetrahedron Lett. 2002, 43, 3237.
20. (c) Reddy, M. A.; Bhanumathi, N.; Rao, K. R. Chem. Commun. 2001, 1974.
21. (d) Reddy, L. R.; Bhanumathi, N.; Rao, K. R. Chem. Commun. 2000, 2321.
22. (e) Reddy, L. R.; Reddy, M. A.; Bhanumathi, N.; Rao, K. R. Synlett 2000, 339.
23. (f) Reddy, M. A.; Reddy, L. R.; Bhanumathi, N.; Rao, K. R. New J. Chem. 2001, 25, 359.
24. (g) Reddy, M. A.; Reddy, L. R.; Bhanumathi, N.; Rao, K. R. Chem. Lett. 2001, 246.
25. Chou, D, T, H.; Zhu, J.; Huang, X.; Bennet, A. J. J. Chem. Soc., Perkin Trans. 2 2001, 83.
26. Tee, O, S.; Hussein, S, M, I.; Turner, I, E.; Yazbeck, O. J. Can. J. Chem. 2000, 78, 436.
27. (a) Lee, S. H.; Lee, J. H.; Yoon, C. M. Tetrahedron Lett. 2002, 43, 2699.
28. (b) Carrigan, M. D.; Sarapa, D.; Smith, R. C.; Wieland, L. C.; Mohan, R. S. J. Org. Chem. 2002, 67, 1027.
29. (c) Reddy, M. A.; Reddy, L. R.; Bhanumathi, N.; Rao, K. R. Synth. Commun. 2002, 32, 273.
30. (a) Clerici, A.; Pastori, N.; Porta, O. Tetrahedron 1998, 54, 15679.
31. (b) Basu, M. K.; Samajdar, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319.
32. (c) Kaur, G.; Trehan, A.; Trehan, S. J. Org. Chem. 1998, 63, 2365.