A practical and efficient procedure for the cleavage of acylals to aldehydes catalyzed by indium tribromide in water

Tetrahedron Letters

Volumn 46, Issue 5, 2005, Pages 889-893

  Zhang, Zhan Hui ^a   Yin, Liang ^a   Li, Yi ^a   Wang, Yong Mei ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Acylals; Aldehydes; Deprotection; Indium tribromide; Protecting groups; Water

Indexed keywords

ALDEHYDE; BENZYL DERIVATIVE; BROMIDE; INDIUM; METHYL GROUP; PLASMALOGEN; WATER;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CATALYST; DEPROTECTION REACTION;

EID: 11844288315     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.161     Document Type: Article

References (53)

1. M. Poliakoff, J.M. Fitzpatrick, T.R. Farren, and P.T. Anastas Science 297 2002 807 810
2. J.M. Desimone Science 297 2002 799 803
3. C.J. Li, and T.H. Chan Organic Reactions in Aqueous Media 1997 Wiley New York
4. G.-J. ten Brink, I.W.C.E. Arends, and R.A. Sheldon Science 287 2000 1636 1639
5. U.M. Lindstroem Chem. Rev. 102 2002 2751 2772
6. R. Breslow Acc. Chem. Res. 24 1991 159 164
7. S. Kobayashi, and K. Manabe Acc. Chem. Res. 35 2002 533 538
8. J.B.F.N. Engberts, and M.J. Blandamer Chem. Commun. 2001 1701 1702
9. S. Kobayashi, and K. Manabe Pure Appl. Chem. 72 2000 1373 1380
10. T.W. Greene, and P.G.M. Wuts Protecting Groups in Organic Synthesis 3rd ed. 1999 Wiley New York
11. D.H. Aggen, J.N. Arnold, P.D. Hayes, N.J. Smoter, and R.S. Mohan Tetrahedron 60 2004 3675 3679
12. A.K. Chakraborti, R. Thilagavathi, and R. Kumar Synthesis 2004 831 833
13. R. Ghosh, S. Maiti, A. Chakraborty, and R. Halder J. Mol. Catal. A: Chem. 215 2004 49 53
14. T.-S. Jin, G.-L. Feng, M.-N. Yang, and T.-S. Li Synth. Commun. 34 2004 1645 1651
15. G. Smitha, and C.S. Reddy Tetrahedron 59 2003 9571 9576
16. G.P. Romanelli, H.J. Thomas, G.T. Baronetti, and J.C. Autino Tetrahedron Lett. 44 2003 1301 1303
17. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, and K. Amani Tetrahedron Lett. 44 2003 3951 3954
18. B. Karimi, and J. Maleki J. Org. Chem. 68 2003 4951 4954
19. B.C. Ranu, J. Dutta, and A. Das Chem. Lett. 32 2003 366 367
20. B.P. Bandgar, S.S. Makone, and S.R. Kularni Monatsh. Chem. 131 2000 417 420
21. F.R. Heerden, J.J. Huyser, D.B.G. Williams, and C.W. Holzapfer Tetrahedron Lett. 39 1998 5281 5284
22. B.M. Trost, and C. Lee J. Am. Chem. Soc. 123 2001 12191 12201
23. K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N. Rajadhyaksha, and H.W. Pinnick J. Org. Chem. 48 1983 1765 1767
24. C. Narayana, S. Padmanabhan, and G.W. Kabalka Tetrahedron Lett. 31 1990 6977 6978
25. P. Cotelle, and J.-P. Catteau Tetrahedron Lett. 33 1992 3855 3858
26. R.S. Varma, A.K. Chatterjee, and M. Varma Tetrahedron Lett. 34 1993 3207 3210
27. G.S. Reddy, R. Radhika, P. Neelakantan, and D.S. Iyengar Indian. J. Chem. 41B 2002 863 864
28. T. Ramalingam, R. Srinivas, B.V.S. Reddy, and J.S. Yadav Synth. Commun. 31 2001 1091 1095
29. M.A. Zolifgol, M.H. Zebarjadian, I. Mohammadpoor-Baltork, and M. Shamsipur Synth. Commun. 32 2002 2803 2808
30. I. Mohammadpoor-Baltork, and H. Alyan J. Chem. Res., Synop. 1999 272 273
31. I. Mohammadpoor-Baltork, and H. Aliyan Synth. Commun. 29 1999 2741 2746
32. V. Aggarwai, S. Fonquerna, and G.P. Vennall Synlett 1998 849 850
33. R. Hosseinzadeh, M. Tajbakhsh, A. Shakoori, and M.Y. Niaki Monatsh. Chem. 135 2004 1243 1249
34. G. Sartori, R. Ballini, F. Bigi, G. Bosica, R. Maggi, and P. Righi Chem. Rev. 104 2004 199 250
35. T.-S. Li, Z.-H. Zhang, and C.-G. Fu Tetrahedron Lett. 38 1997 3285 3288
36. T.-S. Jin, Y.-R. Ma, Z.-H. Zhang, and T.-S. Li Synth. Commun. 27 1997 3379 3383
37. R. Ballini, M. Bordoni, G. Bosica, R. Maggi, and G. Sartori Tetrahedron Lett. 39 1998 7580 7587
38. M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, and M. Nocchetti Tetrahedron Lett. 43 2002 2709 2711
39. B.P. Bandgar, S.P. Kasture, K. Tidke, and S.S. Makone Green. Chem. 2 2000 152 153
40. M.A. Reddy, L.R. Reddy, N. Bhanumathi, and K.R. Rao Synth. Commun. 32 2002 273 277
41. J.S. Yadav, B.V.S. Reddy, and T. Swamy Synthesis 2004 106 110
42. J.S. Yadav, B.V.S. Reddy, and G. Baishya Synlett 2003 396 398
43. J.S. Yadav, B.V.S. Reddy, K.V. Rao, K.S. Raj, and A.R. Prasad Synthesis 2002 1061 1064
44. M. Bandini, P. Melchiorre, A. Melloni, and A. Umani-Ronchi Synthesis 2002 1110 1114
45. J.S. Yadav, B.V.S. Reddy, and G. Parimala Synlett 2002 1143 1145
46. N.-Y. Fu, Y.-H. Yuan, Z. Cao, S.-W. Wang, J.-T. Wang, and C. Peppe Tetrahedron 58 2002 4801 4807
47. M. Agnusdei, M. Bandini, A. Melloni, and A. Umani-Ronchi J. Org. Chem. 68 2003 7126 7129
48. J.S. Yadav, and B.V.S. Reddy Synthesis 2002 511 514
49. M. Bandini, P.G. Cozzi, M. Giacomini, P. Melchiorre, S. Selva, and A. Umani-Ronchi J. Org. Chem. 67 2002 3700 3704
50. M. Banaini, P.G. Cozzi, A. Garelli, P. Melchiorre, and A. Umani-Ronchi Eur. J. Org. Chem. 2002 3243 3249
51. J.S. Yadav, V.S.B. Reddy, M.S. Reddy, and G. Parimala Synthesis 2003 2390 2394
52. L. Yin, Z.-H. Zhang, Y.-M. Wang, and M.-L. Pang Synlett 2004 1727 1730
53. M.J. Gregory J. Chem. Sc. (B) 1970 1201 1207