Dimethylsulfoxide-iodine catalysed deprotection of allyl carboxylic esters

Tetrahedron Letters

Volumn 47, Issue 5, 2006, Pages 643-646

  Taksande, Kiran N ^a   Sakate, Sachin S ^a   Lokhande, Pradeep D ^a  

^a UNIVERSITY OF PUNE   (India)

Author keywords

Allyl ester; Deprotection; Iodine

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DIMETHYL SULFOXIDE; ESTER DERIVATIVE; IODINE; METAL COMPLEX; REAGENT; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; DEPROTECTION REACTION; INTERMETHOD COMPARISON; TECHNIQUE;

EID: 29544446725     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.130     Document Type: Article

References (45)

1. H. Rinderknecht, and V. Ma Helv. Chim. Acta 47 1964 162
2. P.G. Gassman, P.K.G. Hodgson, and R.J. Balchunis J. Am. Chem. Soc. 98 1976 1275
3. A.I. Meyers, and P.J. Reider J. Am. Chem. Soc. 101 1979 2501
4. Reviews: J. Tsuji, and T. Mandai Synthesis 1996 1
5. F. Guibe Tetrahedron 54 1998 2967
6. T.W. Green, and P.G. Wuts Protective Groups in Organic Synthesis 3rd ed. 1979 John Wiley New York
7. N. Ono, M. Tsuboi, S. Okamoto, T. Tanami, and F. Sato Chem. Lett. 1992 2095
8. S. Okamoto, N. Ono, K. Tani, Y. Yoshida, and F. Sato J. Chem. Soc., Chem. Commun. 1994 279
9. V. Schmidt, and B. Rivdl J. Chem. Soc., Chem. Commun. 1992 1186
10. R.W. Hoffmann, and K. Ditrich Liebigs Ann. Chem. 1990 23
11. H. Mastalerz J. Org. Chem. 49 1984 4092
12. E.H. Ruediger, and C. Solomon J. Org. Chem. 56 1991 3183
13. K. Gunnason, L. Grehn, and U. Rangarsson Angew. Chem., Int. Ed. 27 1998 400
14. I. Gill, R. Lopez-Fandino, and E. Vulfson J. Am. Chem. Soc. 117 1995 6175
15. R.J. Jones, and H. Rapoport J. Org. Chem. 55 1990 1144
16. J. Tsuji, and T. Mandai Synthesis 1996 1
17. J. Tsuji Palladium Reagents and Catalysis: Inovation in Organic Synthesis 1995 John Wiley & Sons Chichester
18. J. Tsuji, and T. Yamakawa Tetrahedron Lett. 20 1979 613
19. P.D. Jeffrey, and S.W. McCombie J. Org. Chem. 47 1982 587
20. H. Kautz, and C. Wriverzagt Angew. Chem., Int. Ed. Engl. 23 1984 71
21. H. Zhang, F. Guibe, and G. Balavoine Tetrahedron Lett. 29 1988 619
22. H. Zhang, F. Guibe, and G. Balavoine Tetrahedron Lett. 29 1988 623
23. E.J. Corey, and J. William J. Org. Chem. 38 1973 3223
24. M. Kitamura, S. Tanaka, and M. Yoshimura J. Org. Chem. 67 2002 4975
25. H. Kuntz, and H. Waldmann Helv. Chim. Acta 68 1985 618
26. E.J. Corey, and J. William J. Org. Chem. 38 1973 3224
27. J. Tsuji, T. Yamada, I. Minami, M. Yuhara, M. Nisar, and I. Shimizu J. Org. Chem. 52 1987 2988
28. I. Shimizu, and H. Ishii Tetrahedron 50 1994 487
29. C.R. Schmidt Tetrahedron Lett. 33 1992 757
30. J. Cossy, A. Albouy, M. Scheloske, and D.G. Pardo Tetrahedron Lett. 35 1994 1539
31. A.S. Gajare, N.S. Shaikh, B.K. Bonde, and V.H. Deshpande J. Chem. Soc., Perkin Trans. 1 2000 639
32. B.J. Ghiya, P.A. Soni, and A.G. Doshi Ind. J. Chem. 25B 1986 759
33. F. Wasim, F. Jawaid, W. Manchanda, and R.W. Shaidawara J. Chem. Res. 9 1984 298
34. Waghmare, B. Y. M. Phil. Thesis, University of Pune, Pune, 1998.
35. Gaikwad, D. D. M. Phil. Thesis, University of Pune, Pune, 2003.
36. P.D. Lokahnde, S.S. Sakate, K.N. Taksande, and B. Nawaghare Tetrahedron Lett. 46 2005 1573
37. T. Patonay, J.A.S. Cavaleiro, A. Levai, and A.M.S. Silva Heterocycl. Commun. 3 1997 223
38. M. Singli, and S.K. Grover Ind. J. Chem. 33B 1994 1083
39. D.G. Pinto, A.M.S. Silva, and C.F.F. Cavaleiro Tetrahedron 55 1999 10187
40. W. Tan, W.D. Li, and C. Huang Synth. Commun. 29 1999 3369
41. A.C. Spivey, and R. Srikaran Annu. Rep. Prog. Chem. Sect. B 97 2001 41
42. J.L. Wahlstrom, and R.C. Ronald J. Org. Chem. 63 1998 6021
43. A.R. Mahajan, D.K. Dutta, R.C. Boruah, and J.S. Sandhu Tetrahedron Lett. 31 1990 3943
44. W. Nagata, T. Wakabayashi, M. Narisada, Y. Hayase, and S. Kamata J. Am. Chem. Soc. 93 1971 5740
45. K.H. Kim, M.Y. Park, and S.G. Yang Synlett 3 2002 492