Stereoselective bromohydrin formation from β-hydroxy sulfoxides mediated by the pendant sulfoxide†‡

(Note: The full text of this document is currently only available in the PDF Version )

Sadagopan Raghavan, M. Abdul Rasheed, Suju C. Joseph and A. Rajender


Abstract

Regio- and stereo-selective bromohydrin formation promoted by a neighbouring sulfinyl moiety is disclosed.


References

  1. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Stereoselective Synthesis, Houben-Weyl Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart, 1996, Workbench Edition E 21, vols. 1–10  Search PubMed.
  2. K. Narasaka, Y. Ichikawa and H. Kubota, Chem Lett., 1987, 2139 CAS; The Chemistry of Sulphones and Sulphoxides, ed. S. Patai, Wiley, New York, 1988, pp. 345–346 Search PubMed.
  3. F. Montanari, R. Danieli, H. Hogeveen and G. Maccagnani, Tetrahedron Lett., 1964, 2685 CrossRef CAS.
  4. D. R. Dalton, V. P. Dutta and D. C. Jones, J. Am. Chem. Soc., 1968, 90, 5468.
  5. All new compounds gave satisfactory analytical and spectral data.
  6. G. Solladie, J. Hull and A. Girardin, Synthesis, 1987, 173 CrossRef CAS.
  7. G. I. Tsuchihashi, S. Iriuchijima and M. Ishibashi, Tetrahedron Lett., 1972, 4605 CrossRef CAS; N. Kunieda, M. Kinoshita and J. Nokami, Chem Lett., 1977, 289 CAS; D. R. Williams, J. G. Phillips, F. H. White and J. C. Huffman, Tetrahedron, 1986, 42, 3003 CrossRef CAS; S. G. Pyne and G. Boche, J. Org. Chem., 1989, 54, 2663 CrossRef CAS.
  8. The β-hydroxy sulfoxides 3 and 12 were separated as their silyl ethers followed by cleavage with Bu4NF.
  9. M. C. Carreno, T. L. Garcia Ruano, A. M. Martin, C. Pedregal, J. H. Rodrigues, A. Rubio, J. Sanchez and G. Solladie, J. Org. Chem.,, 1990, 55, 2120 CrossRef CAS and references cited therein C. A. Kingsbury and R. A. Auerbach, J. Org. Chem., 1971, 36, 1737 Search PubMed.
  10. A. D. Westwell, M. Thornton Pett and C. M. Rayner, J. Chem. Soc., Perkin Trans. 1, 1995, 847 RSC; B. M. Trost and M. Fray, Tetrahedron Lett., 1988, 29, 2163 CrossRef CAS.
  11. A. R. Chamberlin, M. Dezube, P. Dussalt and M. C. McMills, J. Am. Chem. Soc., 1983, 105, 5819 CrossRef CAS.
  12. M. M. Midland and R. L. Holtermann, J. Org. Chem., 1981, 46, 1227 CrossRef CAS and references cited therein G. Belluci, G. Berti, R. Bianchini, G. Ingrosso and E. Mastrorilli, Gazz. Chim. Ital.,, 1976, 106, 955 Search PubMed and references cited therein.
  13. S. D. Rychnovsky and D. J. Skalitzky, Tetrahedron Lett., 1990, 31, 945 CrossRef CAS.
  14. G. Dana and H. Danechpajouh, Bull. Soc. Chim. Fr., 1980, 395 CAS.
  15. For instance, the coupling constants for the protons Ha and Hb in 15 is 1.5 Hz, while in 16 it is 9.52 Hz (graphic not included).
  16. P. Sohar, Nuclear Magnetic Resonance Spectroscopy, CRC Press, Florida, 1983, vol. 1, p. 34 Search PubMed; A. B. Foster, T. D. Inch, M. H. Qadir and J. M. Webber, J. Chem. Soc., Chem. Commun., 1968, 1086 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.