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PtCl₄-catalyzed Cycloreorganization of 1,6- and 1,7-Enynes

  • Published : 2003.07.20
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References

  1. Trost, B. M.; Krische, M. J. Synlett 1998, 1.
  2. Mori, M. InTopics in Organometalic Chemistry; Furstner, A., Ed.; Springer-Verlag: Berlin, Heidelberg, 1998; Vol 1, p 133.
  3. Aubert, C.;Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. https://doi.org/10.1021/cr980054f
  4. Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737. https://doi.org/10.1021/ja00289a054
  5. Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110,1636. https://doi.org/10.1021/ja00213a054
  6. Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113,1850. https://doi.org/10.1021/ja00005a070
  7. Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed.Engl. 1993, 32, 1085. https://doi.org/10.1002/anie.199310851
  8. Trost, B. M.; Chang, V. K. Synthesis1993, 824.
  9. Watanuki, S.; Ochifuji, N.; Mori, M. Organometallics 1995,14, 5062. https://doi.org/10.1021/om00011a027
  10. Mori, M.; Watanuki, S. J. Chem. Soc., Chem.Commun. 1992, 1082.
  11. Kinoshita, A.; Mori, M. Synlett 1994, 1020.
  12. Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. https://doi.org/10.1021/jo9616872
  13. Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. https://doi.org/10.1021/ol015606m
  14. Chatani, N.; Furukawa, N.; Sakuri, H.; Murai, S. Organometallics1996, 15, 901. https://doi.org/10.1021/om950832j
  15. Chatani, N.; Inoue, H.; Morimoto, T.;Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433. https://doi.org/10.1021/jo010091y
  16. Chatani, N.;Kataoka, K.; Murai, S.; Rurukawa, N.; Seki, Y. J. Am. Chem. Soc.1998, 120, 9104. https://doi.org/10.1021/ja981877p
  17. Chatani, N.; Morimoto, T.; Muto, T.; Murai,S. J. Am. Chem. Soc. 1994, 116, 6049. https://doi.org/10.1021/ja00092a098
  18. Furstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem.Soc. 1998, 120, 8305 https://doi.org/10.1021/ja981183g
  19. Furstner, A.; Szillat, H.; Stelzer, F. J.Am. Chem. Soc. 2000, 122, 6785. https://doi.org/10.1021/ja001034+
  20. Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics2001, 20, 3704. https://doi.org/10.1021/om010316v
  21. Furstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123,11863. https://doi.org/10.1021/ja0109343
  22. Blum, J.; Beer-Kraft, H.; Badrieh, Y. J. Org. Chem. 1995, 60, 5567. https://doi.org/10.1021/jo00122a043
  23. Kim, S.-H.; Bowden, N.;Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801. https://doi.org/10.1021/ja00102a062
  24. Picquet,C.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 2249.

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  24. Catalytic skeletal reorganization of enynes through electrophilic activation of alkynes: double cleavage of C–C double and triple bonds vol.2009, pp.4, 2009, https://doi.org/10.1039/b812466c
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