Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 979-991
http://dx.doi.org/10.1351/pac200880050979
Palladium-catalyzed selective activation of allyl alcohols as allyl cations, allyl anions, and zwitterionic trimethylenemethanes
References
- 1. Review: Y. Tamaru. Eur. J. Org. Chem. 13, 2647 (2005). (http://dx.doi.org/10.1002/ejoc.200500076)
- 2. Pd-catalyzed formation of allylboranes from allyl alcohols: V. J. Olsson, N. Selander, K. J. Szabo. J. Am. Chem. Soc. 128, 4588 (2006). (http://dx.doi.org/10.1021/ja060468n)
- 3. M. Kimura, M. Futamata, K. Shibata, Y. Tamaru. Chem. Commun. 234 (2003). (http://dx.doi.org/10.1039/b210920d)
- 4. (a). Y. Tamaru, Y. Horino, M. Araki, S. Tanaka, M. Kimura. Tetrahedron Lett. 41, 5705 (2000); (http://dx.doi.org/10.1016/S0040-4039(00)00934-5)
- 4. (b). Y. Horino, M. Naito, M. Kimura, S. Tanaka, Y. Tamaru. Tetrahedron Lett. 42, 3113 (2001); (http://dx.doi.org/10.1016/S0040-4039(01)00381-1)
- 4. (c). M. Mimura, R. Mukai, N. Tanigawa, S. Tanaka, Y. Tamaru. Tetrahedron 59, 7767 (2003). (http://dx.doi.org/10.1016/S0040-4020(03)01234-1)
- 5. M. Kimura, M. Fukasaka, Y. Tamaru. Synthesis 3611 (2006).
- 6. J. Herzig, B. Erthal. Monatsh. Chem. 31, 827 (1910). (http://dx.doi.org/10.1007/BF01530256)
- 7. Surprisingly, 2,2,4,4,6,6-hexaallylcyclohexan-1,3,5-trione is a new compound. This may be due to difficult availability of hexa-alkylation products suggested by ref. [6].
- 8. (a). M. Kimura, M. Futamata, R. Mukai, Y. Tamaru. J. Am. Chem. Soc. 127, 4592 (2005); (http://dx.doi.org/10.1021/ja0501161)
- 8. (b). M. Kimura, M. Fukasaka, Y. Tamaru. Heterocycles 67, 535 (2006).
- 9. B. M. Trost, J. Quancard. J. Am. Chem. Soc. 128, 6314 (2006). (http://dx.doi.org/10.1021/ja0608139)
- 10. Y. Tamaru, M. Kimura, M. Futamata, Y. Shikina. Manuscript in preparation.
- 11. (a). M. S. Morales-Rios, O. R. Suarez-Castillo, J. J. Trujillo-Serrato, P. Joseph-Nathan. J. Org. Chem. 66, 1186 (2001); (http://dx.doi.org/10.1021/jo0012647)
- 11. (b). G. H. Tan, X. Zhu, A. Ganesan. Org. Lett. 5, 1801 (2003); (http://dx.doi.org/10.1021/ol034516+)
- 11. (c). F. Hernandez, C. Avendano, M. Sollhuber. Tetrahedron Lett. 44, 3367 (2003). (http://dx.doi.org/10.1016/S0040-4039(03)00556-2)
- 12. (a). B. M. Trost, E. Keinan. Tetrahedron Lett. 21, 2591 (1980); (http://dx.doi.org/10.1016/S0040-4039(00)92813-2)
- 12. (b). J. Tsuji, I. Minami, I. Shimizu. Chem. Lett. 1325 (1983). (http://dx.doi.org/10.1246/cl.1983.1325)
- 13. K. Hiroi, J. Abe, K. Suya, S. Sato, T. Koyama. J. Org. Chem. 59, 203 (1994). (http://dx.doi.org/10.1021/jo00080a033)
- 14. M. Kimura, Y. Horino, R. Mukai, S. Tanaka, Y. Tamaru. J. Am. Chem. Soc. 123, 10401 (2001). (http://dx.doi.org/10.1021/ja011656a)
- 15. Here, the primary and secondary aldehydes refer to those aldehydes bearing one and two substituents on the C2 of acetaldehyde, respectively.
- 16. (a). H. Harayama, T. Kuroki, M. Kimura, S. Tanaka, Y. Tamaru. Angew. Chem., Int. Ed. Engl. 36, 2352 (1997); (http://dx.doi.org/10.1002/anie.199723521)
- 16. (b). H. Harayama, M. Kimura, S. Tanaka, Y. Tamaru. Tetrahedron Lett. 39, 8475 (1998); (http://dx.doi.org/10.1016/S0040-4039(98)01865-6)
- 16. (c). M. Mori, M. Kimura, Y. Takahashi, Y. Tamaru. Chem. Commun. 4303 (2006). (http://dx.doi.org/10.1039/b610164j)
- 17. M. Kimura, M. Mori, Y. Tamaru. Chem. Commun. 4504 (2007). (http://dx.doi.org/10.1039/b708526e)
- 18. (a). M. Kimura, T. Tomizawa, Y. Horino, S. Tanaka, Y. Tamaru. Tetrahedron Lett. 41, 3627 (2000); (http://dx.doi.org/10.1016/S0040-4039(00)00429-9)
- 18. (b). M. Kimura, M. Shimizu, K. Shibata, M. Tazoe, Y. Tamaru. Angew. Chem., Int. Ed. 42, 3392 (2003); (http://dx.doi.org/10.1002/anie.200351182)
- 18. (c). M. Kimura, M. Shimizu, S. Tanaka, Y. Tamaru. Tetrahedron 61, 3709 (2005); (http://dx.doi.org/10.1016/j.tet.2005.02.005)
- 18. (d). M. Shimizu, M. Kimura, Y. Tamaru. Chem.Eur. J. 11, 6629 (2005). (http://dx.doi.org/10.1002/chem.200500450)
- 19. M. Shimizu, M. Kimura, T. Watanabe, Y. Tamaru. Org. Lett. 7, 637 (2005). (http://dx.doi.org/10.1021/ol047609f)
- 20. Y. Tamaru, M. Kimura, M. Hashimoto. Manuscript in preparation.
- 21. R. Mukai, Y. Horino, S. Tanaka, Y. Tamaru, M. Kimura. J. Am. Chem. Soc. 126, 11138 (2004). (http://dx.doi.org/10.1021/ja0479787)
- 22. (a). B. M. Trost, S. A. King. J. Am. Chem. Soc. 112, 408 (1990); (http://dx.doi.org/10.1021/ja00157a061)
- 22. (b). L. A. Paquette, D. R. Sauer, D. G. Gleary, M. A. Kinsella, C. M. Blackwell, L. G. Anderson. J. Am. Chem. Soc. 114, 7375 (1992); (http://dx.doi.org/10.1021/ja00045a007)
- 22. (c). D. A. Singleton, B. E. Schulmeier. J. Am. Chem. Soc. 121, 9313 (1999); (http://dx.doi.org/10.1021/ja9919229)
- 22. (d). B. M. Trost, M. L. Crawley. J. Am. Chem. Soc. 124, 9328 (2002). (http://dx.doi.org/10.1021/ja026438b)
- 23. H. Nakamura, K. Aoyagi, J.-G. Shim, Y. Yamamoto. J. Am. Chem. Soc. 123, 372 (2001). (http://dx.doi.org/10.1021/ja002931g)
- 24. Y. Tamaru, M. Kimura, T. Watanabe, T. Tamaki. Manuscript submitted for publication.
- 25. B. M. Trost, C. M. Marrs. J. Am. Chem. Soc. 115, 6636 (1993). (http://dx.doi.org/10.1021/ja00068a021)
- 26. M. Kimura, R. Mukai, T. Tamaki, Y. Horino, Y. Tamaru. J. Am. Chem. Soc. 129, 4122 (2007). (http://dx.doi.org/10.1021/ja0687320)