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Tin-free Radical Allylation of α-Acetoxy Alkyl Xanthates. Routes to Homoallyl Alcohols and α,β-Unsaturated Ketones

  • Lee, Jin-Young (Center for Molecular Design & Synthesis and Department of Chemistry, School of Molecular Science (BK-21), Korea Advanced Institute of Science and Technology) ;
  • Kim, Sung-gak (Center for Molecular Design & Synthesis and Department of Chemistry, School of Molecular Science (BK-21), Korea Advanced Institute of Science and Technology)
  • Published : 2006.02.20

Abstract

Keywords

References

  1. Curran, D. P. Synthesis 1988, 489
  2. Rosenstein, I. J. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, p 50
  3. Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron 1985, 41, 4079 https://doi.org/10.1016/S0040-4020(01)97185-6
  4. Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288 https://doi.org/10.1021/ja00212a046
  5. Miura, K.; Itoh, D.; Hondo, T.; Saito, H.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1996, 37, 8539 https://doi.org/10.1016/0040-4039(96)01986-7
  6. Keck, G. E.; Byers, J. H. J. Org. Chem. 1985, 50, 5442 https://doi.org/10.1021/jo00225a107
  7. Curran, D. P.; Yoo, B. Tetrahedron Lett. 1992, 33, 6931 https://doi.org/10.1016/S0040-4039(00)60898-5
  8. Ueno, Y.; Aoki, S.; Okawara, M. J. Chem. Soc., Chem. Commun. 1980, 683
  9. Smith, T. A. K.; Whitham, G. H. Chem. Commun. 1985, 897
  10. Padwa, A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1992, 57, 298 https://doi.org/10.1021/jo00027a052
  11. Chatgilialoglu, C.; Alberti, A.; Ballestri, M.; Macciantelli, D. Tetrahedron Lett. 1996, 37, 6391 https://doi.org/10.1016/0040-4039(96)01355-X
  12. Garner, P.; Leslie, R.; Anderson, J. T. J. Org. Chem. 1996, 61, 6754 https://doi.org/10.1021/jo961499b
  13. Garner, P.; Anderson, J. T. Org. Lett. 1999, 1, 1057 https://doi.org/10.1021/ol990188v
  14. Garner, P.; Anderson, J. T.; Cox, P. B.; Klippenstein, S. J.; Leslie, R.; Scardovi, N. J. Org. Chem. 2002, 67, 6195 https://doi.org/10.1021/jo010880f
  15. Lee, E.; Tae, J. S.; Lee, C.; Park, C. M. Tetrahedron Lett. 1993, 34, 4831 https://doi.org/10.1016/S0040-4039(00)74101-3
  16. Lee, E.; Yoo, S. K.; Choo, H.; Song, H. Y. Tetrahedron Lett. 1998, 39, 317 https://doi.org/10.1016/S0040-4039(97)10555-X
  17. Sibi, M. P.; Zimmerman, J.; Rheault, T. Angew. Chem. Int. Ed. 2003, 42, 4521 https://doi.org/10.1002/anie.200352096
  18. Sibi, M. P.; Patil, K. Org. Lett. 2005, 7, 1453 https://doi.org/10.1021/ol047347h
  19. Appleyard, G. D.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1967, 2686
  20. Ueno, Y.; Ohta, M.; Okawara, M. J. Organomet. Chem. 1980, 197, C1 https://doi.org/10.1016/S0022-328X(00)84448-4
  21. Chou, T. S.; Knochel, P. J. Org. Chem. 1990, 55, 4791 https://doi.org/10.1021/jo00303a007
  22. Sun, S.; Curran, D. P. Tetrahedron Lett. 1991, 32, 6097 https://doi.org/10.1016/0040-4039(91)80762-U
  23. Neuenschwander, M.; Bigler, P.; Christen, K.; Iseli, R.; Kyburz, R.; Muhle, H. Helv. Chim. Acta 1978, 61, 2047 https://doi.org/10.1002/hlca.19780610612
  24. Knochel, P.; Chou, T. S.; Jubert, C.; Rajagopal, D. J. Org. Chem. 1993, 58, 588 https://doi.org/10.1021/jo00055a010
  25. Kim, S.; Lim, C. J. Angew. Chem. Int. Ed. 2002, 41, 3265 https://doi.org/10.1002/1521-3773(20020902)41:17<3265::AID-ANIE3265>3.0.CO;2-X
  26. Kim, S.; Lim, C. J. Bull. Korean Chem. Soc. 2003, 24, 1219 https://doi.org/10.5012/bkcs.2003.24.8.1219
  27. Kim, S.; Lee, S.; Lim, C. J. Bull. Korean Chem. Soc. 2004, 25, 1611 https://doi.org/10.5012/bkcs.2004.25.11.1611
  28. Kim, S.; Kim, S.; Otsuka, N.; Ryu, I. Angew. Chem. 2005, 117, 6339 https://doi.org/10.1002/ange.200501606
  29. Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209 https://doi.org/10.1021/ja9522443
  30. Bertrand, F.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. J. Am. Chem. Soc. 1997, 119, 7410 https://doi.org/10.1021/ja9708878
  31. Zard, S. Z. Angew. Chem. Int. Ed. 1997, 36, 672 https://doi.org/10.1002/anie.199706721
  32. Forbes, J. E.; Zard, S. Z. J. Am. Chem. Soc. 1990, 112, 2034 https://doi.org/10.1021/ja00161a078
  33. Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem. Int. Ed. 1998, 37, 2864 https://doi.org/10.1002/(SICI)1521-3773(19981102)37:20<2864::AID-ANIE2864>3.0.CO;2-W

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