Acetal and ketal deprotection using Montmorillonite K10: The first synthesis of syn-4,8-dioxatricyclo[5.1.0.03,5]-2,6-octanedione

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1881-1884

  Gautier, Elisabeth C L ^a   Graham, Andrew E ^b   McKillop, Alexander ^a   Standen, Stephen P ^b   Taylor, Richard J K ^b  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CARBONYL DERIVATIVE; KETONE DERIVATIVE; MONTMORILLONITE;

ARTICLE; DRUG SYNTHESIS; EPOXIDATION; REACTION ANALYSIS;

EID: 0031575828     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00226-8     Document Type: Article

References (32)

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3. 2. For recent examples see Johnstone, C.; Kerr, W. J.; Scott, J. S. Chem. Commun. 1996, 341; Kantam, M. L.; Swapna, V.; Santhi, P. L. Synth. Commun. 1995, 25, 2529; Caballero, G. M.; Gros, E. G. Synth. Commun. 1995, 25, 395 and references therein.
4. 2. For recent examples see Johnstone, C.; Kerr, W. J.; Scott, J. S. Chem. Commun. 1996, 341; Kantam, M. L.; Swapna, V.; Santhi, P. L. Synth. Commun. 1995, 25, 2529; Caballero, G. M.; Gros, E. G. Synth. Commun. 1995, 25, 395 and references therein.
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8. 5. Cornélls, A.; Laszlo, P.; Zettler, M. W. Encyclopedia of Reagents for Organic Synthesis (p. 3667), Ed. Paquette, L. A., Wiley, Chichester, 1995; Cornélis, A.; Laszlo, P. Synlett 1994, 155 and references therein. For a recent use of this reagent see Shanmugam, P.; Nair, V. Synth. Commun. 1996, 26, 3007.
9. 5. Cornélls, A.; Laszlo, P.; Zettler, M. W. Encyclopedia of Reagents for Organic Synthesis (p. 3667), Ed. Paquette, L. A., Wiley, Chichester, 1995; Cornélis, A.; Laszlo, P. Synlett 1994, 155 and references therein. For a recent use of this reagent see Shanmugam, P.; Nair, V. Synth. Commun. 1996, 26, 3007.
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11. 7. Modified clays have been used to transform selenoacetals, hydrazones, thioacetals and semicarbazones into carbonyl compounds: see Laszlo, P.; Pennetreau, P.; Krief, A. Tetrahedron Lett. 1984, 25, 3153; Laszlo, P.; Polla, E. Tetrahedron Lett. 1984, 25, 3309; Balogh, M.; Cornélls, A.; Laszlo, P. Tetrahedron Lett. 1984, 25, 3313; Laszlo, P.; Polla, E. Synthesis 1985, 439.
12. 7. Modified clays have been used to transform selenoacetals, hydrazones, thioacetals and semicarbazones into carbonyl compounds: see Laszlo, P.; Pennetreau, P.; Krief, A. Tetrahedron Lett. 1984, 25, 3153; Laszlo, P.; Polla, E. Tetrahedron Lett. 1984, 25, 3309; Balogh, M.; Cornélls, A.; Laszlo, P. Tetrahedron Lett. 1984, 25, 3313; Laszlo, P.; Polla, E. Synthesis 1985, 439.
13. 7. Modified clays have been used to transform selenoacetals, hydrazones, thioacetals and semicarbazones into carbonyl compounds: see Laszlo, P.; Pennetreau, P.; Krief, A. Tetrahedron Lett. 1984, 25, 3153; Laszlo, P.; Polla, E. Tetrahedron Lett. 1984, 25, 3309; Balogh, M.; Cornélls, A.; Laszlo, P. Tetrahedron Lett. 1984, 25, 3313; Laszlo, P.; Polla, E. Synthesis 1985, 439.
14. 7. Modified clays have been used to transform selenoacetals, hydrazones, thioacetals and semicarbazones into carbonyl compounds: see Laszlo, P.; Pennetreau, P.; Krief, A. Tetrahedron Lett. 1984, 25, 3153; Laszlo, P.; Polla, E. Tetrahedron Lett. 1984, 25, 3309; Balogh, M.; Cornélls, A.; Laszlo, P. Tetrahedron Lett. 1984, 25, 3313; Laszlo, P.; Polla, E. Synthesis 1985, 439.
15. 8. Professor E. C. Taylor (Princeton University) recently informed us that the effectiveness of K10 for acetal deprotection has also been observed in his laboratory (unpublished results); also see reference 20.
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18. 13C-NMR spectroscopy and by elemental analysis or high resolution mass spectrometry.
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21. 13. The syn-hydroxy diepoxide diastereoisomer of (5) did not undergo deprotection under these conditions but the use of K10 + boron trifluoride etherate gave a good yield of the corresponding ketone (66%).
22. 14. Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101; Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619.
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28. 16. Wollenweber, M.; Hunkler, D.; Keller, M.; Knothe, L.; Prinzbach, H. Bull. Soc. Chim. Fr. 1993, 130, 32; Carman, R. M.; Duffield, A. R.; Lambert, L. K.; Robinson, W. T.; Van Dongen, J. M. A. M. Aust. J. Chem. 1989, 42, 1147; Moore, H. W. J. Org. Chem. 1967, 32, 1996 and references therein.
29. 17. Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. J. K. Unpublished results.
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31. 19. Dr. M. H. Moore (University of York); details will be given in a full paper.
32. 20. A recent comunication described the use of montmorillonite K10 in aqueous methanol for the removal of isopropylidene groups from protected carbohydrates (Asakura, J.; Robins, M. J.; Asaka, Y.; Kim, T. H. J. Org. Chem. 1996, 61, 9026).