Activation of 1,3-dioxolane by a protic ionic liquid in aqueous media: A green strategy for the selective hydrolytic cleavage of acetals and ketals

RSC Advances

Volumn 4, Issue 32, 2014, Pages 16497-16502

  Majumdar, Swapan ^a   Chakraborty, Mithun ^a   Maiti, Dilip K ^b   Chowdhury, Sandip ^c   Hossain, Jewel ^a  

^a TRIPURA UNIVERSITY   (India)

^b UNIVERSITY OF CALCUTTA   (India)

^c INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUPS;

BENZYLIDENE ACETALS; GLYCOSIDIC LINKAGES; HYDROLYTIC CLEAVAGE; MILD REACTION CONDITIONS; PROTIC IONIC LIQUIDS; REACTION CONDITIONS; SELECTIVE DEPROTECTION; TERT-BUTYL ESTERS;

IONIC LIQUIDS;

EID: 84898002229     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra00870g     Document Type: Article

References (55)

1. T. W. Green and P. G. Wuts, in Protective groups in Organic Synthesis, Wiley Inter-science, New York, 1999
2. P. J. Kocienski, in Protecting Groups, Georg Thieme Verlag, New York, 2000
3. M. Nakamura H. Isobe E. Najamura Chem. Rev. 2003 103 1295
4. X. Xiao D. Bai Synlett 2001 535
5. S. E. Sen S. L. Roach J. K. Boggs G. J. Ewing J. J. Magarth J. Org. Chem. 1997 62 6684
6. K. J. Eash M. S. Pulia L. C. Wieland R. S. Mohan J. Org. Chem. 2000 65 8399
7. G. Sabitha R. S. Babu E. V. Reddy J. S. Yadav Chem. Lett. 2000 9 1074
8. N. Komatsu A. Taniguchi S. Wada H. Suzuki Adv. Synth. Catal. 2001 343 473
9. M. D. Carrigan D. Sarapa R. C. Smith L. C. Wieland R. S. Mohan J. Org. Chem. 2002 67 1027
10. R. Dalpozzo A. De Nino L. Maiuolo A. Procopio A. Tagarelli G. Sindona G. Bartoli J. Org. Chem. 2002 67 9093
11. N. Mailide J.-C. Vanherck A. Gautier I. E. Marko Acc. Chem. Res. 2007 40 381
12. G. Sarton R. Magg Chem. Rev. 2004 104 199
13. H. Fujioka T. Okitsu Y. Sawama N. Murata R. Li Y. Kita J. Am. Chem. Soc. 2006 128 5930
14. S. Majumdar A. Bhattacharjya J. Org. Chem. 1999 64 5682
15. T. Welton Chem. Rev. 1999 99 2071
16. P. Wasserscheid W. Keim Angew. Chem., Int. Ed. 2000 39 3772
17. J. S. Wilkes Green Chem. 2002 4 73
18. V. I. Parvulescu C. Hardacre Chem. Rev. 2007 107 2615
19. J.-I. Kadokawa, in Ionic Liquids-New Aspects for the Future, Intech Publisher, 2013
20. M. A. McHugh and V. J. Krukonis, Supercritical Fluid Extraction Principles and Practice, Butterworth-Heinemann, Boston, 2nd edn, 1993
21. L. T. Taylor, in Supercritical Fluid Extraction, John Wiley, New York, 1996
22. A. S. Gopalan, C. M. Wai and H. K. Jacobs, in Supercritical Carbon Dioxide: Separations and Processes, ACS Symposium Series 860, 2003
23. E. Kiran, P. G. Debenedetti and C. J. Peters, in Supercritical Fluids Fundamentals and Applications, Kluwer, Dordrecht, 2000
24. D. E. Knox Pure Appl. Chem. 2005 77 513
25. M. J. Earle P. B. McCormac K. R. Seddon Chem. Commun. 1998 2245
26. F. Liu M. B. Abrams R. T. Baker W. Tumas Chem. Commun. 2001 433
27. E. D. Bates R. D. Mayton I. Ntai J. H. Davis J. Am. Chem. Soc. 2001 124 926
28. J. M. Xu Q. Wu Q. Y. Zhang F. Zhang X. F. Lin Eur. J. Org. Chem. 2007 1798
29. B. C. Ranu A. Saha R. Dey Curr. Opin. Drug Discovery Dev. 2010 13 658
30. A. K. Chakraborti S. Raha Roy J. Am. Chem. Soc. 2009 131 6902
31. S. Majumdar J. De J. Hossain A. Basak Tetrahedron Lett. 2013 54 262
32. J. Venkatraman S. C. Shankaramma P. Balaram Chem. Rev. 2001 101 3131
33. M. C. Khosla K. Stachowiak R. R. Smeby F. M. Bumpus F. Piriou K. Lintner S. Fermandjian Proc. Natl. Acad. Sci. U. S. A. 1981 78 757
34. S. J. O'Connor Z. Liu Synlett 2003 2135
35. M. Tanaka Chem. Pharm. Bull. 2007 55 349
36. T. Kawabata, Asymmetric Synthesis of Amino Acids with a Tetrasubstituted Carbon Center via Memory of Chirality, ACS Symposium Series 1009, 2009
37. G. Zhao T. Jiang H. Gao B. Han J. Huang D. Sun Green Chem. 2004 6 75
38. S.-H. Chen Q. Zhao X.-W. Xu J. Chem. Sci. 2008 120 481
39. A. R. Hajipour F. Rafiee Org. Prep. Proced. Int. 2010 42 285
40. A. R. Hajipour F. Rafiee J. Iran. Chem. Soc. 2009 6 647
41. J.-P. Belieres C. A. Angell J. Phys. Chem. B 2007 111 4926
42. S. Park R. J. Kazlauskas Curr. Opin. Biotechnol. 2003 14 432
43. T. L. Greaves C. J. Drummond Chem. Rev. 2008 108 206
44. S. Majumdar A. Bhattacharjya A. Patra Tetrahedron 1999 55 12157
45. G. V. M. Sharma I. S. Reddy V. G. Reddy A. V. Rama Rao Tetrahedron: Asymmetry 1999 10 229
46. V. K. Rajput B. Roy B. Mukhopadyay Tetrahedron Lett. 2006 47 6987
47. N. D. Vetter D. M. Langill S. Anjum J. Boisvert-Martel R. C. Jagdhane E. Omene H. Zheng K. E. van Straaten I. Asiamah E. S. Krol D. A. R. Sanders D. R. J. Palmer J. Am. Chem. Soc. 2013 135 5970
48. M. Popsavin V. Popsavin N. Vukojevic D. Miljkovic Collect. Czech. Chem. Commun. 1994 59 1884
49. M. Popsavin S. Grabez I. Krstic M. Popsavin D. Djokovic J. Serb. Chem. Soc. 2003 68 795
50. M. Ohlin R. Johnsson U. Ellervik Carbohydr. Res. 2011 346 1358
51. G. Agnihotri A. K. Misra Tetrahedron Lett. 2006 47 3653
52. P. S. Kumar G. D. K. Kumar S. Baskaran Eur. J. Org. Chem. 2008 6063
53. A. Santra T. Ghosh A. K. Misra Beilstein J. Org. Chem. 2013 9 74
54. Y. J. Kim R. S. Varma Tetrahedron Lett. 2005 46 1467
55. Y. J. Kim R. S. Varma Tetrahedron Lett. 2005 46 7447