"Green" oxidation reactions - Application to carbohydrate chemistry

Green Chemistry

Volumn 5, Issue 6, 2003, Pages 679-681

  Boyd, Ewan C ^a   Jones, Ray V H ^a   Quayle, Peter ^b   Waring, Anita J ^b  

^a JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE DERIVATIVE; ALPHA MANNOSIDASE; CARBOHYDRATE; GLUCOPYRANOSIDE; GLYCOSIDE; HYDROGEN PEROXIDE; METHANOL; PEROXIDE; PYRANOSIDE; REAGENT; RHENIUM COMPLEX;

ARTICLE; BIOTRANSFORMATION; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMISTRY; OXIDATION; PRECURSOR; STEREOCHEMISTRY;

EID: 0345829163     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b310207f     Document Type: Article

References (54)

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13. W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149 For the original peparartion of MTO see: I. R. Beattie and P. J. Jones, Inorg. Chem., 1979, 18, 2318 For a detailed experimental procedure see: W. A. Herrmann, R. M. Kratzer, J. H. Espenson and W. Wang, Inorg. Synth., 2002, 33, 110 MTO is now commercially available (Aldrich).
14. W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149 For the original peparartion of MTO see: I. R. Beattie and P. J. Jones, Inorg. Chem., 1979, 18, 2318 For a detailed experimental procedure see: W. A. Herrmann, R. M. Kratzer, J. H. Espenson and W. Wang, Inorg. Synth., 2002, 33, 110 MTO is now commercially available (Aldrich).
15. W. A. Herrmann, J. Organomet. Chem., 1995, 500, 149 For the original peparartion of MTO see: I. R. Beattie and P. J. Jones, Inorg. Chem., 1979, 18, 2318 For a detailed experimental procedure see: W. A. Herrmann, R. M. Kratzer, J. H. Espenson and W. Wang, Inorg. Synth., 2002, 33, 110 MTO is now commercially available (Aldrich).
16. J. H. Espenson, Chem. Commun., 1999, 479; W. Adam, M. C. Mitchell, R. C. Saha-Möller and O. Weichold, Struct. Bonding (Berlin), 2000, 97, 237; F. E. Kuhn and W. A. Herrmann, Struct. Bonding (Berlin), 2000, 97, 213 For recent investigations see: G. S. Owens, A. Durazo and M. M. Abu-Omar, Chem. Eur. J., 2002, 8, 3053; R. Saladino, V. Neri, A. R. Pelliccia, R. Anna, R. Caminiti and C. Sadun, J. Org. Chem., 2002, 67, 1323; J. Iskra, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2002, 43, 1001; R. Saladino, V. Neri, E. Mincione and P. Filippone, Tetrahedron, 2002, 58, 8493 For aerobic transformations see: V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 3235; V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 2655.
17. J. H. Espenson, Chem. Commun., 1999, 479; W. Adam, M. C. Mitchell, R. C. Saha-Möller and O. Weichold, Struct. Bonding (Berlin), 2000, 97, 237; F. E. Kuhn and W. A. Herrmann, Struct. Bonding (Berlin), 2000, 97, 213 For recent investigations see: G. S. Owens, A. Durazo and M. M. Abu-Omar, Chem. Eur. J., 2002, 8, 3053; R. Saladino, V. Neri, A. R. Pelliccia, R. Anna, R. Caminiti and C. Sadun, J. Org. Chem., 2002, 67, 1323; J. Iskra, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2002, 43, 1001; R. Saladino, V. Neri, E. Mincione and P. Filippone, Tetrahedron, 2002, 58, 8493 For aerobic transformations see: V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 3235; V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 2655.
18. J. H. Espenson, Chem. Commun., 1999, 479; W. Adam, M. C. Mitchell, R. C. Saha-Möller and O. Weichold, Struct. Bonding (Berlin), 2000, 97, 237; F. E. Kuhn and W. A. Herrmann, Struct. Bonding (Berlin), 2000, 97, 213 For recent investigations see: G. S. Owens, A. Durazo and M. M. Abu-Omar, Chem. Eur. J., 2002, 8, 3053; R. Saladino, V. Neri, A. R. Pelliccia, R. Anna, R. Caminiti and C. Sadun, J. Org. Chem., 2002, 67, 1323; J. Iskra, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2002, 43, 1001; R. Saladino, V. Neri, E. Mincione and P. Filippone, Tetrahedron, 2002, 58, 8493 For aerobic transformations see: V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 3235; V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 2655.
19. J. H. Espenson, Chem. Commun., 1999, 479; W. Adam, M. C. Mitchell, R. C. Saha-Möller and O. Weichold, Struct. Bonding (Berlin), 2000, 97, 237; F. E. Kuhn and W. A. Herrmann, Struct. Bonding (Berlin), 2000, 97, 213 For recent investigations see: G. S. Owens, A. Durazo and M. M. Abu-Omar, Chem. Eur. J., 2002, 8, 3053; R. Saladino, V. Neri, A. R. Pelliccia, R. Anna, R. Caminiti and C. Sadun, J. Org. Chem., 2002, 67, 1323; J. Iskra, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2002, 43, 1001; R. Saladino, V. Neri, E. Mincione and P. Filippone, Tetrahedron, 2002, 58, 8493 For aerobic transformations see: V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 3235; V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 2655.
20. J. H. Espenson, Chem. Commun., 1999, 479; W. Adam, M. C. Mitchell, R. C. Saha-Möller and O. Weichold, Struct. Bonding (Berlin), 2000, 97, 237; F. E. Kuhn and W. A. Herrmann, Struct. Bonding (Berlin), 2000, 97, 213 For recent investigations see: G. S. Owens, A. Durazo and M. M. Abu-Omar, Chem. Eur. J., 2002, 8, 3053; R. Saladino, V. Neri, A. R. Pelliccia, R. Anna, R. Caminiti and C. Sadun, J. Org. Chem., 2002, 67, 1323; J. Iskra, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2002, 43, 1001; R. Saladino, V. Neri, E. Mincione and P. Filippone, Tetrahedron, 2002, 58, 8493 For aerobic transformations see: V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 3235; V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 2655.
21. J. H. Espenson, Chem. Commun., 1999, 479; W. Adam, M. C. Mitchell, R. C. Saha-Möller and O. Weichold, Struct. Bonding (Berlin), 2000, 97, 237; F. E. Kuhn and W. A. Herrmann, Struct. Bonding (Berlin), 2000, 97, 213 For recent investigations see: G. S. Owens, A. Durazo and M. M. Abu-Omar, Chem. Eur. J., 2002, 8, 3053; R. Saladino, V. Neri, A. R. Pelliccia, R. Anna, R. Caminiti and C. Sadun, J. Org. Chem., 2002, 67, 1323; J. Iskra, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2002, 43, 1001; R. Saladino, V. Neri, E. Mincione and P. Filippone, Tetrahedron, 2002, 58, 8493 For aerobic transformations see: V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 3235; V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 2655.
22. J. H. Espenson, Chem. Commun., 1999, 479; W. Adam, M. C. Mitchell, R. C. Saha-Möller and O. Weichold, Struct. Bonding (Berlin), 2000, 97, 237; F. E. Kuhn and W. A. Herrmann, Struct. Bonding (Berlin), 2000, 97, 213 For recent investigations see: G. S. Owens, A. Durazo and M. M. Abu-Omar, Chem. Eur. J., 2002, 8, 3053; R. Saladino, V. Neri, A. R. Pelliccia, R. Anna, R. Caminiti and C. Sadun, J. Org. Chem., 2002, 67, 1323; J. Iskra, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2002, 43, 1001; R. Saladino, V. Neri, E. Mincione and P. Filippone, Tetrahedron, 2002, 58, 8493 For aerobic transformations see: V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 3235; V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 2655.
23. J. H. Espenson, Chem. Commun., 1999, 479; W. Adam, M. C. Mitchell, R. C. Saha-Möller and O. Weichold, Struct. Bonding (Berlin), 2000, 97, 237; F. E. Kuhn and W. A. Herrmann, Struct. Bonding (Berlin), 2000, 97, 213 For recent investigations see: G. S. Owens, A. Durazo and M. M. Abu-Omar, Chem. Eur. J., 2002, 8, 3053; R. Saladino, V. Neri, A. R. Pelliccia, R. Anna, R. Caminiti and C. Sadun, J. Org. Chem., 2002, 67, 1323; J. Iskra, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2002, 43, 1001; R. Saladino, V. Neri, E. Mincione and P. Filippone, Tetrahedron, 2002, 58, 8493 For aerobic transformations see: V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 3235; V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 2655.
24. J. H. Espenson, Chem. Commun., 1999, 479; W. Adam, M. C. Mitchell, R. C. Saha-Möller and O. Weichold, Struct. Bonding (Berlin), 2000, 97, 237; F. E. Kuhn and W. A. Herrmann, Struct. Bonding (Berlin), 2000, 97, 213 For recent investigations see: G. S. Owens, A. Durazo and M. M. Abu-Omar, Chem. Eur. J., 2002, 8, 3053; R. Saladino, V. Neri, A. R. Pelliccia, R. Anna, R. Caminiti and C. Sadun, J. Org. Chem., 2002, 67, 1323; J. Iskra, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2002, 43, 1001; R. Saladino, V. Neri, E. Mincione and P. Filippone, Tetrahedron, 2002, 58, 8493 For aerobic transformations see: V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 3235; V. B. Sharma, S. L. Jain and B. Sain, Tetrahedron Lett., 2003, 44, 2655.
25. For seminal work in this area see: (a) R. L. Halcomb and S. J. Danishefsky, J. Am. Chem. Soc., 1989, 111, 6661; (b) S. J. Danishefsky and J. R. Allen, Angew. Chem., Int. Ed. Engl., 2000, 39, 836; L. J. Williams, R. M. Garbaccio and S. J. Danishefsky in Carbohydr. Chem. Biol., 2000, 1, 61. Wiley-VCH Verlag GmbH, Weinheim, ed. R. Ernst and P. Sinäy.
26. For seminal work in this area see: (a) R. L. Halcomb and S. J. Danishefsky, J. Am. Chem. Soc., 1989, 111, 6661; (b) S. J. Danishefsky and J. R. Allen, Angew. Chem., Int. Ed. Engl., 2000, 39, 836; L. J. Williams, R. M. Garbaccio and S. J. Danishefsky in Carbohydr. Chem. Biol., 2000, 1, 61. Wiley-VCH Verlag GmbH, Weinheim, ed. R. Ernst and P. Sinäy.
27. For seminal work in this area see: (a) R. L. Halcomb and S. J. Danishefsky, J. Am. Chem. Soc., 1989, 111, 6661; (b) S. J. Danishefsky and J. R. Allen, Angew. Chem., Int. Ed. Engl., 2000, 39, 836; L. J. Williams, R. M. Garbaccio and S. J. Danishefsky in Carbohydr. Chem. Biol., 2000, 1, 61. Wiley-VCH Verlag GmbH, Weinheim, ed. R. Ernst and P. Sinäy.
28. (a) H. Tan and J. H. Espenson, Inorg. Chem., 1998, 37, 467;
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48. (b) H. R. Tetzlaff and J. H. Espenson, Inorg. Chem, 1999, 38, 881 For theoretical studies see: C. Di Valentin, R. Gandolfi, P. Gisdakis and N. Rösch, J. Am. Chem. Soc., 2001, 123, 2365.
49. See ref. 10a for the generation of α,β-unsaturated ketones from allylic alcohols using this reagent.
50. 2,2-dichloro-2-deoxy-D-arabinohexose is known, see: J. Adamson and A. B. Foster, Carbohydr. Res., 1969, 10, 517 See: M. M. Abu-Omar and J. H. Espenson, Organometallics, 1996, 15, 3543 for a related reaction.
51. 2,2-dichloro-2-deoxy-D-arabinohexose is known, see: J. Adamson and A. B. Foster, Carbohydr. Res., 1969, 10, 517 See: M. M. Abu-Omar and J. H. Espenson, Organometallics, 1996, 15, 3543 for a related reaction.
52. See: W. Adam and C. M. Mitchell, Angew. Chem., Int. Edn. Engl., 1996, 35, 533; D. Musumeci and D. Sica, Steroids, 2002, 67, 661.
53. See: W. Adam and C. M. Mitchell, Angew. Chem., Int. Edn. Engl., 1996, 35, 533; D. Musumeci and D. Sica, Steroids, 2002, 67, 661.
54. We presume that acetamide is also produced as a by-product in this oxidation sequence but we were unable to verify its generation because of its water solubility.