Sulfur oxidation in supercritical carbon dioxide: Dramatic pressure dependant enhancement of diastereoselectivity for sulfoxidation of cysteine derivatives

Chemical Communications

Volumn , Issue 3, 1999, Pages 247-248

  Oakes, R Scott ^a   Clifford, Anthony A ^a   Bartle, Keith D ^a   Pett, Mark Thornton ^a   Rayner, Christopher M ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CYSTEINE; CYSTEINE DERIVATIVE; ION EXCHANGE RESIN; METHIONINE; SOLVENT; SULFIDE; SULFOXIDE; SULFUR; TERT BUTYL HYDROPEROXIDE;

ARTICLE; OXIDATION; PRESSURE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0033531359     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. A. A. Clifford, Fundamentals of Supercritical Fluids, Oxford University Press, 1998; A. A. Clifford, in Supercritical Fluids, ed. E. Kiran and J. M. H. Levelt Sengers, Kluwer, Dordrecht, 1994, p. 449.
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3. See for example: L. E. McMahon, P. Timmins, A. C. Williams and P. York. J. Pharm. Sci., 1996, 85, 1064; J. W. Tom, G. B. Lim, P. G. Debendetti and R. K. Prud'homme, in Supercritical Fluid Engineering Science - Fundamentals and Applications, ed. E. Kiran and J. F. Brennecke, ACS Symp. Ser. 514, 1993, ch. 11; P. G. Debendetti, Supercritical Fluids, ed. E. Kiran and J. M. H. Levelt Sengers, Kluwer, Dordrecht, 1994, p. 719.
4. See for example: L. E. McMahon, P. Timmins, A. C. Williams and P. York. J. Pharm. Sci., 1996, 85, 1064; J. W. Tom, G. B. Lim, P. G. Debendetti and R. K. Prud'homme, in Supercritical Fluid Engineering Science - Fundamentals and Applications, ed. E. Kiran and J. F. Brennecke, ACS Symp. Ser. 514, 1993, ch. 11; P. G. Debendetti, Supercritical Fluids, ed. E. Kiran and J. M. H. Levelt Sengers, Kluwer, Dordrecht, 1994, p. 719.
5. See for example: L. E. McMahon, P. Timmins, A. C. Williams and P. York. J. Pharm. Sci., 1996, 85, 1064; J. W. Tom, G. B. Lim, P. G. Debendetti and R. K. Prud'homme, in Supercritical Fluid Engineering Science - Fundamentals and Applications, ed. E. Kiran and J. F. Brennecke, ACS Symp. Ser. 514, 1993, ch. 11; P. G. Debendetti, Supercritical Fluids, ed. E. Kiran and J. M. H. Levelt Sengers, Kluwer, Dordrecht, 1994, p. 719.
6. For recent examples see: M. A. Carroll and A. B. Holmes, Chem. Commun., 1998, 1395; D. K. Morita, D. R. Pesiri, S. A. David, W. H. Glaze and W. Tumas, Chem. Commun., 1998, 1397; M. G. Hitzler, F. R. Small, S. K. Ross and M. Poliakoff, Chem. Commun., 1998, 359; D. R. Pesiri, D. K. Morita, W. Glaze and W. Tumas, Chem. Commun., 1998, 1015; G. R. Haas and J. W. Kollis, Tetrahedron Lett., 1998, 39, 5923.
7. For recent examples see: M. A. Carroll and A. B. Holmes, Chem. Commun., 1998, 1395; D. K. Morita, D. R. Pesiri, S. A. David, W. H. Glaze and W. Tumas, Chem. Commun., 1998, 1397; M. G. Hitzler, F. R. Small, S. K. Ross and M. Poliakoff, Chem. Commun., 1998, 359; D. R. Pesiri, D. K. Morita, W. Glaze and W. Tumas, Chem. Commun., 1998, 1015; G. R. Haas and J. W. Kollis, Tetrahedron Lett., 1998, 39, 5923.
8. For recent examples see: M. A. Carroll and A. B. Holmes, Chem. Commun., 1998, 1395; D. K. Morita, D. R. Pesiri, S. A. David, W. H. Glaze and W. Tumas, Chem. Commun., 1998, 1397; M. G. Hitzler, F. R. Small, S. K. Ross and M. Poliakoff, Chem. Commun., 1998, 359; D. R. Pesiri, D. K. Morita, W. Glaze and W. Tumas, Chem. Commun., 1998, 1015; G. R. Haas and J. W. Kollis, Tetrahedron Lett., 1998, 39, 5923.
9. For recent examples see: M. A. Carroll and A. B. Holmes, Chem. Commun., 1998, 1395; D. K. Morita, D. R. Pesiri, S. A. David, W. H. Glaze and W. Tumas, Chem. Commun., 1998, 1397; M. G. Hitzler, F. R. Small, S. K. Ross and M. Poliakoff, Chem. Commun., 1998, 359; D. R. Pesiri, D. K. Morita, W. Glaze and W. Tumas, Chem. Commun., 1998, 1015; G. R. Haas and J. W. Kollis, Tetrahedron Lett., 1998, 39, 5923.
10. For recent examples see: M. A. Carroll and A. B. Holmes, Chem. Commun., 1998, 1395; D. K. Morita, D. R. Pesiri, S. A. David, W. H. Glaze and W. Tumas, Chem. Commun., 1998, 1397; M. G. Hitzler, F. R. Small, S. K. Ross and M. Poliakoff, Chem. Commun., 1998, 359; D. R. Pesiri, D. K. Morita, W. Glaze and W. Tumas, Chem. Commun., 1998, 1015; G. R. Haas and J. W. Kollis, Tetrahedron Lett., 1998, 39, 5923.
11. A. A. Clifford, K. Pople, W. J. Gaskill, K. D. Bartle and C. M. Rayner, J. Chem. Soc., Faraday Trans., 1998, 94, 1451.
12. R. S. Oakes, A. A. Clifford, K. D. Bartle, and C. M. Rayner, unpublished results.
13. Other sulfonic acid-based catalysts have been reported: F. Bonadies, F. De Angelis, L. Locati and S. Scettri, Tetrahedron Lett., 1996, 37, 7129; G. W. Breton, J. D. Fields and P. J. Kropp, Tetrahedron Lett., 1995, 36, 3825.
14. Other sulfonic acid-based catalysts have been reported: F. Bonadies, F. De Angelis, L. Locati and S. Scettri, Tetrahedron Lett., 1996, 37, 7129; G. W. Breton, J. D. Fields and P. J. Kropp, Tetrahedron Lett., 1995, 36, 3825.
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18. Variable selectivities (up to 88% de) have been reported for the oxidation of N-protected β-amino phenyl sulfides using TEMPO and sodium hypochlorite, see: R. Siedlecka and J. Skarzewski, Synlett, 1996, 757; A. Lewanowicz, J. Lipinski, R. Siedlecka, J. Skarzewski and F. Baert, Tetrahedron, 1998, 54, 6571.
19. Variable selectivities (up to 88% de) have been reported for the oxidation of N-protected β-amino phenyl sulfides using TEMPO and sodium hypochlorite, see: R. Siedlecka and J. Skarzewski, Synlett, 1996, 757; A. Lewanowicz, J. Lipinski, R. Siedlecka, J. Skarzewski and F. Baert, Tetrahedron, 1998, 54, 6571.
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