Synthesis of α-diazo-β-oxo sulfoxides

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2819-2822

  Maguire, Anita R ^c   Kelleher, Patrick G ^c   Ferguson, George ^a   Gallagher, John F ^a,b  

^a UNIVERSITY OF GUELPH   (Canada)

^b DUBLIN CITY UNIVERSITY   (Ireland)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA DIAZO BETA OXO SULFOXIDE; CEPHALOSPORIN DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONJUGATION; DRUG STABILITY; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0032580420     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00255-X     Document Type: Article

References (29)

1. 1. Ye, T.; McKervey, M.A. Chem. Rev., 1994, 94, 1091; Padwa, A.; Krumpe, K.E. Tetrahedron, 1992, 48, 5385; Padwa, A.; Weingarten, M.D. Chem. Rev., 1996, 96, 223.
2. 1. Ye, T.; McKervey, M.A. Chem. Rev., 1994, 94, 1091; Padwa, A.; Krumpe, K.E. Tetrahedron, 1992, 48, 5385; Padwa, A.; Weingarten, M.D. Chem. Rev., 1996, 96, 223.
3. 1. Ye, T.; McKervey, M.A. Chem. Rev., 1994, 94, 1091; Padwa, A.; Krumpe, K.E. Tetrahedron, 1992, 48, 5385; Padwa, A.; Weingarten, M.D. Chem. Rev., 1996, 96, 223.
4. 2. Monteiro, H.J. Tetrahedron Lett., 1987, 28, 3459; Kennedy, M.; McKervey, M.A.; Maguire, A.R.; Roos, G.H.P. J. Chem. Soc., Chem. Commun., 1990, 361; Miller, D.J.; Moody, C.J. Tetrahedron, 1995, 51, 10811.
5. 2. Monteiro, H.J. Tetrahedron Lett., 1987, 28, 3459; Kennedy, M.; McKervey, M.A.; Maguire, A.R.; Roos, G.H.P. J. Chem. Soc., Chem. Commun., 1990, 361; Miller, D.J.; Moody, C.J. Tetrahedron, 1995, 51, 10811.
6. 2. Monteiro, H.J. Tetrahedron Lett., 1987, 28, 3459; Kennedy, M.; McKervey, M.A.; Maguire, A.R.; Roos, G.H.P. J. Chem. Soc., Chem. Commun., 1990, 361; Miller, D.J.; Moody, C.J. Tetrahedron, 1995, 51, 10811.
7. 3. Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Chem. Comm., 1976, 538; Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Perkin Trans. I, 1977, 2298; Ebbinghaus, C.F.; Morrissey, P.; Rosati, R.L. J. Org. Chem., 1979, 44, 4697; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Bordner, J.; Subramanian, E. J. Am. Chem. Soc., 1982, 104, 4262; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Retsema, J.A. J. Med. Chem., 1990, 33, 291
8. 3. Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Chem. Comm., 1976, 538; Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Perkin Trans. I, 1977, 2298; Ebbinghaus, C.F.; Morrissey, P.; Rosati, R.L. J. Org. Chem., 1979, 44, 4697; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Bordner, J.; Subramanian, E. J. Am. Chem. Soc., 1982, 104, 4262; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Retsema, J.A. J. Med. Chem., 1990, 33, 291
9. 3. Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Chem. Comm., 1976, 538; Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Perkin Trans. I, 1977, 2298; Ebbinghaus, C.F.; Morrissey, P.; Rosati, R.L. J. Org. Chem., 1979, 44, 4697; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Bordner, J.; Subramanian, E. J. Am. Chem. Soc., 1982, 104, 4262; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Retsema, J.A. J. Med. Chem., 1990, 33, 291
10. 3. Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Chem. Comm., 1976, 538; Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Perkin Trans. I, 1977, 2298; Ebbinghaus, C.F.; Morrissey, P.; Rosati, R.L. J. Org. Chem., 1979, 44, 4697; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Bordner, J.; Subramanian, E. J. Am. Chem. Soc., 1982, 104, 4262; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Retsema, J.A. J. Med. Chem., 1990, 33, 291
11. 3. Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Chem. Comm., 1976, 538; Bremner, D.H.; Campbell, M.M. J. Chem. Soc., Perkin Trans. I, 1977, 2298; Ebbinghaus, C.F.; Morrissey, P.; Rosati, R.L. J. Org. Chem., 1979, 44, 4697; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Bordner, J.; Subramanian, E. J. Am. Chem. Soc., 1982, 104, 4262; Rosati, R.L.; Kapili, L.V.; Morrissey, P.; Retsema, J.A. J. Med. Chem., 1990, 33, 291
12. 4. Franck-Neumann, M.; Lohmann, J.J. Tetrahedron Lett., 1979, 2397.
13. 5. Lammert, S.R.; Kukolja, S. J. Am. Chem. Soc., 1975, 97, 5583; Ayca, E. Rev. fac. sci. univ. Istanbul Ser. C, 1957, 22, 371, Chem. Abs., 1959, 53, 11287f; Venier, C.G.; Gibbs, C.G.; Tetrahedron Lett., 1972, 2293; Venier, C.G.; Hsieh, H.-H.; Barager, H.J. J. Org. Chem., 1973, 38, 17; Venier, C.G.; Barager, H.J. J. Chem. Soc., Chem. Comm., 1973, 319; Venier, C.G.; Barager, H.J.; Ward, M.A. J. Am. Chem. Soc., 1975, 97, 3238; Venier, C.G.; Ward, M.A. Tetrahedron Lett., 1978, 3215.
14. 5. Lammert, S.R.; Kukolja, S. J. Am. Chem. Soc., 1975, 97, 5583; Ayca, E. Rev. fac. sci. univ. Istanbul Ser. C, 1957, 22, 371, Chem. Abs., 1959, 53, 11287f; Venier, C.G.; Gibbs, C.G.; Tetrahedron Lett., 1972, 2293; Venier, C.G.; Hsieh, H.-H.; Barager, H.J. J. Org. Chem., 1973, 38, 17; Venier, C.G.; Barager, H.J. J. Chem. Soc., Chem. Comm., 1973, 319; Venier, C.G.; Barager, H.J.; Ward, M.A. J. Am. Chem. Soc., 1975, 97, 3238; Venier, C.G.; Ward, M.A. Tetrahedron Lett., 1978, 3215.
15. 5. Lammert, S.R.; Kukolja, S. J. Am. Chem. Soc., 1975, 97, 5583; Ayca, E. Rev. fac. sci. univ. Istanbul Ser. C, 1957, 22, 371, Chem. Abs., 1959, 53, 11287f; Venier, C.G.; Gibbs, C.G.; Tetrahedron Lett., 1972, 2293; Venier, C.G.; Hsieh, H.-H.; Barager, H.J. J. Org. Chem., 1973, 38, 17; Venier, C.G.; Barager, H.J. J. Chem. Soc., Chem. Comm., 1973, 319; Venier, C.G.; Barager, H.J.; Ward, M.A. J. Am. Chem. Soc., 1975, 97, 3238; Venier, C.G.; Ward, M.A. Tetrahedron Lett., 1978, 3215.
16. 5. Lammert, S.R.; Kukolja, S. J. Am. Chem. Soc., 1975, 97, 5583; Ayca, E. Rev. fac. sci. univ. Istanbul Ser. C, 1957, 22, 371, Chem. Abs., 1959, 53, 11287f; Venier, C.G.; Gibbs, C.G.; Tetrahedron Lett., 1972, 2293; Venier, C.G.; Hsieh, H.-H.; Barager, H.J. J. Org. Chem., 1973, 38, 17; Venier, C.G.; Barager, H.J. J. Chem. Soc., Chem. Comm., 1973, 319; Venier, C.G.; Barager, H.J.; Ward, M.A. J. Am. Chem. Soc., 1975, 97, 3238; Venier, C.G.; Ward, M.A. Tetrahedron Lett., 1978, 3215.
17. 5. Lammert, S.R.; Kukolja, S. J. Am. Chem. Soc., 1975, 97, 5583; Ayca, E. Rev. fac. sci. univ. Istanbul Ser. C, 1957, 22, 371, Chem. Abs., 1959, 53, 11287f; Venier, C.G.; Gibbs, C.G.; Tetrahedron Lett., 1972, 2293; Venier, C.G.; Hsieh, H.-H.; Barager, H.J. J. Org. Chem., 1973, 38, 17; Venier, C.G.; Barager, H.J. J. Chem. Soc., Chem. Comm., 1973, 319; Venier, C.G.; Barager, H.J.; Ward, M.A. J. Am. Chem. Soc., 1975, 97, 3238; Venier, C.G.; Ward, M.A. Tetrahedron Lett., 1978, 3215.
18. 5. Lammert, S.R.; Kukolja, S. J. Am. Chem. Soc., 1975, 97, 5583; Ayca, E. Rev. fac. sci. univ. Istanbul Ser. C, 1957, 22, 371, Chem. Abs., 1959, 53, 11287f; Venier, C.G.; Gibbs, C.G.; Tetrahedron Lett., 1972, 2293; Venier, C.G.; Hsieh, H.-H.; Barager, H.J. J. Org. Chem., 1973, 38, 17; Venier, C.G.; Barager, H.J. J. Chem. Soc., Chem. Comm., 1973, 319; Venier, C.G.; Barager, H.J.; Ward, M.A. J. Am. Chem. Soc., 1975, 97, 3238; Venier, C.G.; Ward, M.A. Tetrahedron Lett., 1978, 3215.
19. 5. Lammert, S.R.; Kukolja, S. J. Am. Chem. Soc., 1975, 97, 5583; Ayca, E. Rev. fac. sci. univ. Istanbul Ser. C, 1957, 22, 371, Chem. Abs., 1959, 53, 11287f; Venier, C.G.; Gibbs, C.G.; Tetrahedron Lett., 1972, 2293; Venier, C.G.; Hsieh, H.-H.; Barager, H.J. J. Org. Chem., 1973, 38, 17; Venier, C.G.; Barager, H.J. J. Chem. Soc., Chem. Comm., 1973, 319; Venier, C.G.; Barager, H.J.; Ward, M.A. J. Am. Chem. Soc., 1975, 97, 3238; Venier, C.G.; Ward, M.A. Tetrahedron Lett., 1978, 3215.
20. 5. Lammert, S.R.; Kukolja, S. J. Am. Chem. Soc., 1975, 97, 5583; Ayca, E. Rev. fac. sci. univ. Istanbul Ser. C, 1957, 22, 371, Chem. Abs., 1959, 53, 11287f; Venier, C.G.; Gibbs, C.G.; Tetrahedron Lett., 1972, 2293; Venier, C.G.; Hsieh, H.-H.; Barager, H.J. J. Org. Chem., 1973, 38, 17; Venier, C.G.; Barager, H.J. J. Chem. Soc., Chem. Comm., 1973, 319; Venier, C.G.; Barager, H.J.; Ward, M.A. J. Am. Chem. Soc., 1975, 97, 3238; Venier, C.G.; Ward, M.A. Tetrahedron Lett., 1978, 3215.
21. 6. Hodson, D.; Holt, G. J. Chem. Soc. (C), 1968, 1602. Decomposition of α-diazo-β-keto sulfoxides by oxygen transfer from sulfur to carbon to form the α-keto acid thiol esters was proposed.
22. 7. Satisfactory spectroscopic and analytical / HRMS data was obtained for all new compounds
23. 8. Sulfoxide 2 was synthesised by oxidation of a mixture of the cis and trans sulfides 1 and 4 with oxone®, followed by chromatographic separation of the resulting sulfoxides 2. 5 and 6. Sulfoxides 5 and 6 were prepared by oxidation (mCPBA) ot the trans sulfide 4 followed by chromatographic separation. Full details of the investigation of the oxidation of the sulfides 1, 4, 9 and 12 will be reported elsewhere.
24. 9. The sulfides were prepared following standard procedures: for 1 and 4 see Koskimies, J.K. Acta Chem. Scand. B, 1984, 3, 101, for 9 and 12 see Garcia Ruano, J.L.; Martinez, M.C.; Rodriguez, I.H.; Olefirowicz, E.M.; Eliel, E.L. J. Org. Chem., 1992, 57, 4215.
25. 9. The sulfides were prepared following standard procedures: for 1 and 4 see Koskimies, J.K. Acta Chem. Scand. B, 1984, 3, 101, for 9 and 12 see Garcia Ruano, J.L.; Martinez, M.C.; Rodriguez, I.H.; Olefirowicz, E.M.; Eliel, E.L. J. Org. Chem., 1992, 57, 4215.
26. 10. Hazen, G.G.; Bollinger, F.W.; Roberts, F.E.; Russ, W.K.; Seman, J.J.; Staskiewicz, S. Org. Synth., 1995, 73, 144; Bollinger, F.W.; Tuma, L.D. Synlett, 1996, 407.
27. 10. Hazen, G.G.; Bollinger, F.W.; Roberts, F.E.; Russ, W.K.; Seman, J.J.; Staskiewicz, S. Org. Synth., 1995, 73, 144; Bollinger, F.W.; Tuma, L.D. Synlett, 1996, 407.
28. 3S requires 214.0412.
29. 2 data. All non-H atoms were allowed anisotropic motion. All H atoms were visible in difference maps and allowed for as riding atoms. Full details of molecular dimensions, fractional coordinates, thermal parameters and structure factor listing are available from the authors and have been deposited with the Cambridge Crystallographic Data Centre.