Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Stannylcarbonylation of Hydroxy-substituted Alkynes. Intramoleuclar Trapping of α-Ketenyl Radicals by a Hydroxy Group Leading to Lactols

  • Ryu, Il-Hyong (Department of Chemistry, Graduate School of Science, Osaka Prefecture University) ;
  • Fukuyama, Takahide (Department of Chemistry, Graduate School of Science, Osaka Prefecture University) ;
  • Nobuta, Osamu (Department of Chemistry, Graduate School of Science, Osaka Prefecture University) ;
  • Uenoyama, Yoshitaka (Department of Chemistry, Graduate School of Science, Osaka Prefecture University)
  • Published : 2010.03.20
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References

  1. Ryu, I.; Sonoda, N. Angew. Chem. Int. Ed. Engl. 1996, 35, 1050. https://doi.org/10.1002/anie.199610501
  2. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. https://doi.org/10.1021/cr9400626
  3. Ryu, I. Chem. Soc. Rev. 2001, 30, 16. https://doi.org/10.1039/a904591k
  4. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991. https://doi.org/10.1021/cr9601425
  5. Ryu, I.; Uenoyama, Y.; Matsubara, H. Bull. Chem. Soc. Jpn. 2006, 79, 1476. https://doi.org/10.1246/bcsj.79.1476
  6. Matsubara, H.; Ryu, I.; Schiesser, C. H. J. Org. Chem. 2005, 70, 3610. https://doi.org/10.1021/jo047868i
  7. Ryu, I.; Miyazato, H.; Kuriyama, K.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632. https://doi.org/10.1021/ja034896u
  8. Tojino, M.; Otsuka, N.; Fukuyama, T.; Matsubara, H.; Schiesser, C. H.; Kuriyama, H.; Miyazato, H.; Minakata, S.; Komatsu, M.; Ryu, I. Org. Biomol. Chem. 2003, 1, 4262. https://doi.org/10.1039/b309944j
  9. Tojino, M.; Uenoyama, Y.; Fukuyama, T.; Ryu, I. Chem. Commun. 2004, 2482.
  10. Uenoyama, Y.; Fukuyama, T.; Nobuta, O.; Matsubara, H.; Ryu, I. Angew. Chem. Int. Ed. 2005, 44, 1075. https://doi.org/10.1002/anie.200461954
  11. Tojino, M.; Otsuka, N.; Fukuyama, T.; Matsubara, H.; Ryu, I. J. Am. Chem. Soc. 2006, 128, 7712. https://doi.org/10.1021/ja0623865
  12. Uenoyama, Y.; Fukuyama, T.; Ryu, I. Org. Lett. 2007, 9, 935. https://doi.org/10.1021/ol070080c
  13. Nishii, Y.; Nagano, T.; Gotoh, H.; Nagase, R.; Motoyoshiya, J.; Aoyama, H.; Tanabe, Y. Org. Lett. 2007, 9, 563. https://doi.org/10.1021/ol062673d
  14. Duffy, L. A.; Matsubara, H.; Procter, D. J. J. Am. Chem. Soc. 2008, 130, 1136. https://doi.org/10.1021/ja078137d
  15. Parmar, D.; Duffy, L. A.; Sadasivam, D. V.; Matsubara, H.; Bradley, P. A.; Flowers, R. A. II; Procter, D. J. J. Am. Chem. Soc. 2009, 131, 15467. https://doi.org/10.1021/ja906396u
  16. Studer, A.; Amrein, S.; Matsubara, H.; Schiesser, C. H.; Doi, T.; Kawamura, T.; Fukuyama, T.; Ryu, I. Chem. Commun. 2003, 1190.
  17. Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. https://doi.org/10.1021/ja00013a081
  18. Kim, S.; Lim, K. M. Tetrahedron Lett. 1993, 34, 4851. https://doi.org/10.1016/S0040-4039(00)74107-4
  19. Kim, S.; Horvat, S. M.; Schiesser, C. H. Aust. J. Chem. 2002, 55, 753. https://doi.org/10.1071/CH02147
  20. Chang, S.-Y.; Shao, Y.-F.; Chu, S.-F.; Fan, G.-T.; Tsai, Y.-M. Org. Lett. 1999, 1, 945. https://doi.org/10.1021/ol990199o
  21. Ueng, S.-H.; Chen, M.-J.; Chu, S.-F.; Shao, Y.-F.; Fan, G.-T.; Chang, S.-Y.; Tsai, Y.-M. J. Org. Chem. 2006, 71, 1502. https://doi.org/10.1021/jo052176v

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