Remarkably efficient deprotection of cyclic acetals and ketals

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1799-1802

  Ates, Ali ^a   Gautier, Arnaud ^a   Leroy, Bernard ^a   Plancher, Jean Marc ^a   Quesnel, Yannick ^a   Markó, István E ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; CERIUM AMMONIUM NITRATE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; ORGANIC CHEMISTRY; QUANTITATIVE ASSAY; REACTION ANALYSIS; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 0033605164     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00013-1     Document Type: Article

References (25)

1. 1. Ates, A.; Markó, I.E. Manuscript in preparation.
2. 2. For some leading references, see: (a) Barton, D.H.R.; Akhtar, M. J. Am. Chem. Soc., 1964, 86, 1528.
3. (b) Suarez, E.; Conception, J.I.; Francisco, C.G.; Hernandez, R.; Salazard, J.A. Tetrahedron Lett., 1984, 25, 1953.
4. (c) Arigoni, D.; Cainelli, G.; Mihailovic, M.L.; Jeger, O. Helv. Chim. Acta, 1959, 42, 1124.
5. (d) Walling, C.; Padwa, A. J. Am. Chem. Soc., 1961, 83, 2207.
6. (e) Barton, D.H.R.; Beaton, J.M.; Geller, L.E.; Peclet, M.M. J. Am. Chem. Soc., 1961, 83, 4076.
7. (f) Suarez, E.; Francisco, C.G.; Leone, E.I.; Moreno, P. Tetrahedron Asymmetry, 1998, 9, 2975.
8. 3. (a) Ho, T.-L. Cerium(IV) Oxidation of Organic Compounds in Organic Syntheses by Oxidation with Metal Compounds; Mijs, W.J.; deJonge, C.R.H.I. Eds., Plenum Press, New York, 1986.
9. (b) Trahanovsky, W.S.; Young, M.G.; Nave, P.M. Tetrahedron Lett., 1969, 10, 2501.
10. (c) Ho, T.-L. Synthesis, 1973, 347.
11. 4. Remarkably, epimerisation of the cis-fused decaline 3 into the more stable trans-isomei did not occur under these reaction conditions.
12. 5. Ho, T.-L.; Ho, C.H.; Wong, C.M. J. Chem. Soc., Chem. Commun., 1972, 791.
13. 6. DattaGupta, A.; Singh, R.; Singh, V.K. Synlett, 1996, 69.
14. 7. Hwu, J.R.; Jain, M.L.; Tsay, S.-C.; Hakimelahi, G.H. Tetrahedron Lett., 1996, 37, 2035.
15. 8. For other deprotections using CAN, see for example: (a) Matsumoto, T.; Katsuki, M.; Jona, H.; Suzuki, K. J. Am. Chem. Soc., 1991, 113, 6982.
16. (b) Schreiber, S.L.; Kiessling, L.L. Tetrahedron Lett., 1989, 30, 433.
17. (c) Choi, J.-R.; Han, S.; Cha, J.K. Tetrahedron Lett., 1991, 32, 6469.
18. (d) Cotelle, P.; Catteau, J.-P. Tetrahedron Lett., 1992, 33, 3855.
19. 9. The discrepancy in yields between the crude products and the analytically pure compounds mostly reflects the mechanical losses encountered during the purification step. The crude products are sufficiently pure (>95% purity) to be used directly in a subsequent transformation.
20. 3, see: Marcantoni, E.; Nobili, F.; Bartoli, G.; Bosco, M.; Sambri, L. J. Org. Chem., 1997, 62, 4183.
21. 3CN solvent. For substrates that are highly sensitive to acidic conditions, a borate buffer (pH = 8) can be successfully employed (see Table 1, Entry 4).
22. 12. For electron-transfer reactions using CAN, see for example: Baciocchi, E.; Giacco, T.D.; Rol, C.; Sebastiani, G.V. Tetrahedron Lett., 1989, 30, 3573.
23. 3CN mixture. For the formation of red-coloured complexes between CAN and alcohols, see: (a) Young, L.B.; Trahanovsky, W.S. J. Am. Chem. Soc., 1969, 91, 5060.
24. (b) Littler, J.-S.; Waters, W.A. J. Chem. Soc., 1960, 2767.
25. 2: C, 71.39; H, 9.59. Found: C, 70.93; H, 9.70.