Radical-chain reductive carboxyalkylation of electron-rich alkenes: carbon–carbon bond formation mediated by silanes in the presence of thiols as polarity-reversal catalysts

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Hai-Shan Dang, Kyoung-Mahn Kim and Brian P. Roberts


Abstract

The reductive carboxyalkylation of electron-rich alkenes by α-halogenoesters in the presence of triphenylsilane under free-radical conditions is catalysed by thiols: prochiral alkenes give optically-active adducts when the thiol catalyst is homochiral.


References

  1. B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986 Search PubMed; W. B. Motherwell and D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992 Search PubMed.
  2. P. Pike, S. Hershberger and J. Hershberger, Tetrahedron Lett., 1985, 26, 6289 CrossRef CAS.
  3. B. Giese, B. Kopping and C. Chatgilialoglu, Tetrahedron Lett., 1989, 30, 681 CrossRef CAS.
  4. B. Giese, H. Horler and M. Leising, Chem. Ber., 1986, 119, 444 CAS; T. F. Herpin, W. B. Motherwell and M. J. Tozer, Tetrahedron: Asymmetry, 1994, 5, 2269 CrossRef CAS.
  5. V. Paul and B. P. Roberts, J. Chem. Soc., Chem. Commun., 1987, 1322 RSC; V. Paul and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1988, 1183 RSC; H.-S. Dang and B. P. Roberts, J. Chem. Soc., Perkin Trans. 1, 1993, 891 RSC.
  6. (a) R. P. Allen, B. P. Roberts and C. R. Willis, J. Chem. Soc., Chem. Commun., 1989, 1387 RSC; (b) J. N. Kirwan, B. P. Roberts and C. R. Willis, Tetrahedron Lett., 1990, 31, 5093 CrossRef CAS; (c) S. J. Cole, J. N. Kirwan, B. P. Roberts and C. R. Willis, J. Chem. Soc., Perkin Trans. 1, 1991, 103 RSC; (d) H.-S. Dang and B. P. Roberts, Tetrahedron Lett., 1995, 36, 2875 CrossRef CAS; (e) M. B. Haque and B. P. Roberts, Tetrahedron Lett., 1996, 37, 9123 CrossRef CAS; (f) H.-S. Dang and B. P. Roberts, J. Chem. Soc., Perkin Trans. 1, 1998, 67 RSC.
  7. B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2155 RSC; B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1996, 2719 RSC.
  8. H. Kiefer and T. G. Traylor, Tetrahedron Lett., 1966, 6163 CrossRef CAS; G. D. Mendenhall, Tetrahedron Lett., 1983, 24, 451 CrossRef CAS.
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