Remarkable deprotection of THP and THF ethers catalysed by cerium ammonium nitrate (CAN) under neutral conditions

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5613-5616

  Markó, István E ^a   Ates, Ali ^a   Augustyns, Benoît ^a   Gautier, Arnaud ^a   Quesnel, Yannick ^a   Turet, Laurent ^a   Wiaux, Marianne ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMMONIUM NITRATE; BORIC ACID; CERIUM NITRATE; ETHER DERIVATIVE; TETRAHYDROFURANYL ETHER; TETRAHYDROPYRANYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 0033166815     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01043-6     Document Type: Article

References (27)

1. (a) Greene, T.W.; Wuts, P.G.M. In Protective Groups in Organic Chemistry, John Wiley & Sons, Inc., New-York, 1991, Chapter 4.
2. (b) Kocienski, P.J. in Protecting Groups, Georg Thieme Verlag, New-York, 1994.
3. (a) Miyashita, M; Yoshikoshi, A.; Grieco, P. J. Org. Chem., 1977, 42, 3772-3774.
4. (b) Corey, E. J.; Niwa, H.; Knolle, J. J. Am. Chem. Soc., 1978, 100, 1942-1943.
5. (c) Bernardy, K.; Floyd, M.B.; Poletto, J.F.; Weiss, M.J. J. Org. Chem., 1979, 44, 1438-1447.
6. (d) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett., 1984, 25, 663-664.
7. (e) Fadel, A.; Salaun, J. Tetrahedron, 1985, 41, 1267-1275.
8. (f) Gala, D.; Steinman, M.; Jaret, R.S. J. Org. Chem., 1986, 51, 4488-4490.
9. (g) Kim, S.; Park, J.H. Tetrahedron Lett., 1987, 28, 439-440.
10. (h) Johnston, R.D.; Marston, C.R.; Krieger, P.E.; Goe, G.L. Synthesis, 1988, 393-394.
11. (i) Nambiar, K.P.; Mitra, A. Tetrahedron Lett., 1994, 35, 3033-3036.
12. (j) Zimmermann, K. Synth. Commun., 1995, 25, 2959-2962.
13. (k) Lee, A.S.-Y.; Su, F.-Y.; Liao, Y.-C. Tetrahedron Lett., 1999, 40, 1323-1326.
14. Ates, A.; Gautier, A.; Leroy, B.; Plancher, J.-M.; Quesnel, Y.; Markó, I.E. Tetrahedron Lett. 1999, 40, 1799-1802.
15. For some leading references, see: (a) Ho, T.-L. in Cerium(IV) Oxidation of Organic Compounds in Organic Synthesis by Oxidation with Metal Compounds, (Eds.: Mijs, W.J.; deJonge, C.R.H.I.), Plenum Press, New-York, 1986.
16. (b) Ho, T.-L.; Ho, C.H.; Wong, C.M. J. Chem. Soc., Chem. Commun. 1972, 791.
17. (c) T.-L. Ho, Synthesis, 1978, 936.
18. (d) Olah, G.A.; Gupta, B.G.B.; Fung, A.P. Synthesis, 1980, 897-898.
19. (e) Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett., 1982, 23, 539-542.
20. (f) Schreiber, S.L.; Kiesling, L.L. Tetrahedron Lett. 1989, 30, 433.
21. (g) Matsumoto, T.; Katsuki, M.; Jona, H.; Suzuki, K. J. Am. Chem. Soc. 1991, 113, 6982.
22. (h) Cotelle, P.; Catteau, J.-P. Tetrahedron Lett. 1992, 33, 3855.
23. (i) DattaGupta, A.; Singh, R.; Singh, V.K. Synlett. 1996, 69.
24. (j) Hwu, J.R.; Jain, M.L.; Tsay, S.-C.; Hakimelahi, G.H. Tetrahedron Lett. 1996, 37, 2035.
25. Markó, I.E.; Ates, A.; Gautier, A.; Leroy, B.; Plancher, J.-M.; Quesnel, Y.; Vanheerck, J.-C. Angew. Chem., Int. Ed. Engl., 1999, submitted.
26. The deprotection of THP ethers using a modified CAN derivative has been reported: Iranpoor, N.; Salehi, P. Iran. J. Chem. & Chem. Eng., 1996, 15, 8-10. Under these conditions, however, acid-catalysed cleavage of the acetal cannot be ruled out.
27. 2O) m/z. (relative intensity) 163 (20%), 161 (60%).