Use of an organometallic reagent in water: Sc(OTf)3-catalyzed allylation reactions of aldehydes in micellar systems

Chemistry Letters

Volumn , Issue 8, 1997, Pages 831-832

  Kobayashi, Shu ^a   Wakabayashi, Takeshi ^a   Oyamada, Hidekazu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031518949     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.831     Document Type: Article

References (31)

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3. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379; S. Kobayashi, H. Ishitani, and S. Nagayama, Synthesis, 1995, 1195; H. Ishitani, S. Nagayama, and S. Kobayashi, J. Org. Chem., 61, 1902 (1996); S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 118, 8977 (1996); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996); S. Kobayashi, M. Moriwaki, and I. Hachiya, Bull. Chem. Soc. Jpn., 70, 267 (1997); S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997), and references cited therein.
4. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379; S. Kobayashi, H. Ishitani, and S. Nagayama, Synthesis, 1995, 1195; H. Ishitani, S. Nagayama, and S. Kobayashi, J. Org. Chem., 61, 1902 (1996); S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 118, 8977 (1996); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996); S. Kobayashi, M. Moriwaki, and I. Hachiya, Bull. Chem. Soc. Jpn., 70, 267 (1997); S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997), and references cited therein.
5. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379; S. Kobayashi, H. Ishitani, and S. Nagayama, Synthesis, 1995, 1195; H. Ishitani, S. Nagayama, and S. Kobayashi, J. Org. Chem., 61, 1902 (1996); S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 118, 8977 (1996); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996); S. Kobayashi, M. Moriwaki, and I. Hachiya, Bull. Chem. Soc. Jpn., 70, 267 (1997); S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997), and references cited therein.
6. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379; S. Kobayashi, H. Ishitani, and S. Nagayama, Synthesis, 1995, 1195; H. Ishitani, S. Nagayama, and S. Kobayashi, J. Org. Chem., 61, 1902 (1996); S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 118, 8977 (1996); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996); S. Kobayashi, M. Moriwaki, and I. Hachiya, Bull. Chem. Soc. Jpn., 70, 267 (1997); S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997), and references cited therein.
7. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379; S. Kobayashi, H. Ishitani, and S. Nagayama, Synthesis, 1995, 1195; H. Ishitani, S. Nagayama, and S. Kobayashi, J. Org. Chem., 61, 1902 (1996); S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 118, 8977 (1996); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996); S. Kobayashi, M. Moriwaki, and I. Hachiya, Bull. Chem. Soc. Jpn., 70, 267 (1997); S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997), and references cited therein.
8. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379; S. Kobayashi, H. Ishitani, and S. Nagayama, Synthesis, 1995, 1195; H. Ishitani, S. Nagayama, and S. Kobayashi, J. Org. Chem., 61, 1902 (1996); S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 118, 8977 (1996); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996); S. Kobayashi, M. Moriwaki, and I. Hachiya, Bull. Chem. Soc. Jpn., 70, 267 (1997); S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997), and references cited therein.
9. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379; S. Kobayashi, H. Ishitani, and S. Nagayama, Synthesis, 1995, 1195; H. Ishitani, S. Nagayama, and S. Kobayashi, J. Org. Chem., 61, 1902 (1996); S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 118, 8977 (1996); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996); S. Kobayashi, M. Moriwaki, and I. Hachiya, Bull. Chem. Soc. Jpn., 70, 267 (1997); S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997), and references cited therein.
10. Review: Y. Yamamoto and N. Asao, Chem. Rev., 93, 2207 (1993).
11. I. Hachiya and S. Kobayashi, J. Org. Chem., 58, 6958 (1993); S. Kobayashi, I. Hachiya, and Y. Yamanoi, Bull. Chem. Soc. Jpn., 67, 2342 (1994).
12. I. Hachiya and S. Kobayashi, J. Org. Chem., 58, 6958 (1993); S. Kobayashi, I. Hachiya, and Y. Yamanoi, Bull. Chem. Soc. Jpn., 67, 2342 (1994).
13. As for utility of aqueous reactions, see, C.-J. Li, Chem. Rev., 93, 2023 (1993);
14. A. Lubineau, J. Ange, and Y. Queneau, Synthesis, 1994, 741;
15. "Structure and Reactivity in Aqueous Solution", eds by C. J. Cramer and D. G. Truhlar, ACS, Washington, DC (1994).
16. S. Kobayashi, T. Wakabayashi, S. Nagayama, and H. Oyamada, Tetrahedron Lett., in press.
17. Cf. J. H. Fendler and E. J. Fendler, "Catalysis in Micellar and Macromolecular Systems," Academic Press, London (1975); "Mixed Surfactant Systems," eds by P. M. Holland and D. N. Rubingh, ACS, Washington, DC (1994); "Surfactant-Enhanced Subsurface Remediation," eds by D. A. Sabatini, R. C. Knox, and J. H. Harwell, ACS, Washington, DC (1995).
18. Cf. J. H. Fendler and E. J. Fendler, "Catalysis in Micellar and Macromolecular Systems," Academic Press, London (1975); "Mixed Surfactant Systems," eds by P. M. Holland and D. N. Rubingh, ACS, Washington, DC (1994); "Surfactant-Enhanced Subsurface Remediation," eds by D. A. Sabatini, R. C. Knox, and J. H. Harwell, ACS, Washington, DC (1995).
19. Cf. J. H. Fendler and E. J. Fendler, "Catalysis in Micellar and Macromolecular Systems," Academic Press, London (1975); "Mixed Surfactant Systems," eds by P. M. Holland and D. N. Rubingh, ACS, Washington, DC (1994); "Surfactant-Enhanced Subsurface Remediation," eds by D. A. Sabatini, R. C. Knox, and J. H. Harwell, ACS, Washington, DC (1995).
20. As for allylation using tetraallyltin, W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); D. N. Harpp and M. Gingras, J. Am. Chem. Soc., 110, 7737 (1988); S. Fukuzawa, K. Sato, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1990, 939; A. Yanagisawa, H. Inoue, M. Morodome, and H. Yamamoto, J. Am. Chem. Soc., 115, 10356 (1993); T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, and D. J. Young, J. Org. Chem., 62, 1961 (1997). See also, M. Yasuda, Y. Sugawa, A. Yamamoto, I. Shibata, and A. Baba, Tetrahedron Lett., 37, 5951 (1996).
21. As for allylation using tetraallyltin, W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); D. N. Harpp and M. Gingras, J. Am. Chem. Soc., 110, 7737 (1988); S. Fukuzawa, K. Sato, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1990, 939; A. Yanagisawa, H. Inoue, M. Morodome, and H. Yamamoto, J. Am. Chem. Soc., 115, 10356 (1993); T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, and D. J. Young, J. Org. Chem., 62, 1961 (1997). See also, M. Yasuda, Y. Sugawa, A. Yamamoto, I. Shibata, and A. Baba, Tetrahedron Lett., 37, 5951 (1996).
22. As for allylation using tetraallyltin, W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); D. N. Harpp and M. Gingras, J. Am. Chem. Soc., 110, 7737 (1988); S. Fukuzawa, K. Sato, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1990, 939; A. Yanagisawa, H. Inoue, M. Morodome, and H. Yamamoto, J. Am. Chem. Soc., 115, 10356 (1993); T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, and D. J. Young, J. Org. Chem., 62, 1961 (1997). See also, M. Yasuda, Y. Sugawa, A. Yamamoto, I. Shibata, and A. Baba, Tetrahedron Lett., 37, 5951 (1996).
23. As for allylation using tetraallyltin, W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); D. N. Harpp and M. Gingras, J. Am. Chem. Soc., 110, 7737 (1988); S. Fukuzawa, K. Sato, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1990, 939; A. Yanagisawa, H. Inoue, M. Morodome, and H. Yamamoto, J. Am. Chem. Soc., 115, 10356 (1993); T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, and D. J. Young, J. Org. Chem., 62, 1961 (1997). See also, M. Yasuda, Y. Sugawa, A. Yamamoto, I. Shibata, and A. Baba, Tetrahedron Lett., 37, 5951 (1996).
24. As for allylation using tetraallyltin, W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); D. N. Harpp and M. Gingras, J. Am. Chem. Soc., 110, 7737 (1988); S. Fukuzawa, K. Sato, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1990, 939; A. Yanagisawa, H. Inoue, M. Morodome, and H. Yamamoto, J. Am. Chem. Soc., 115, 10356 (1993); T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, and D. J. Young, J. Org. Chem., 62, 1961 (1997). See also, M. Yasuda, Y. Sugawa, A. Yamamoto, I. Shibata, and A. Baba, Tetrahedron Lett., 37, 5951 (1996).
25. As for allylation using tetraallyltin, W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); D. N. Harpp and M. Gingras, J. Am. Chem. Soc., 110, 7737 (1988); S. Fukuzawa, K. Sato, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1990, 939; A. Yanagisawa, H. Inoue, M. Morodome, and H. Yamamoto, J. Am. Chem. Soc., 115, 10356 (1993); T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, and D. J. Young, J. Org. Chem., 62, 1961 (1997). See also, M. Yasuda, Y. Sugawa, A. Yamamoto, I. Shibata, and A. Baba, Tetrahedron Lett., 37, 5951 (1996).
26. As for allylation using tetraallyltin, W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); D. N. Harpp and M. Gingras, J. Am. Chem. Soc., 110, 7737 (1988); S. Fukuzawa, K. Sato, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1990, 939; A. Yanagisawa, H. Inoue, M. Morodome, and H. Yamamoto, J. Am. Chem. Soc., 115, 10356 (1993); T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, and D. J. Young, J. Org. Chem., 62, 1961 (1997). See also, M. Yasuda, Y. Sugawa, A. Yamamoto, I. Shibata, and A. Baba, Tetrahedron Lett., 37, 5951 (1996).
27. Salicylaldehyde has a free hydroxy group which is incompatible with metal enolates or Lewis acids, and 2-pyridinecarboxaldehyde is generally difficult to use under the influence of Lewis acids because of the coordination of the nitrogen atom to the Lewis acids resulting in the deactivation of the acids
28. W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); T. H. Chan and M. B. Isaac, Pure Appl. Chem., 68, 919 (1996).
29. W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 113, 6674 (1991); T. H. Chan and M. B. Isaac, Pure Appl. Chem., 68, 919 (1996).
30. Judging from the critical micelle concentration, micelles would be formed in these reactions.
31. When TritonX-100 was used as a surfactant, the anion exchange resin treatment was not needed.