Lewis acid catalysis in aqueous media: Copper(II)-catalyzed aldol and allylation reactions in a water-ethanol-toluene solution

Chemistry Letters

Volumn , Issue 9, 1997, Pages 959-960

  Kobayashi, Shu ^a   Nagayama, Satoshi ^a   Busujima, Tsuyoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031321768     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.959     Document Type: Article

References (36)

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22. A. Lubineau, J. Org. Chem., 51, 2142 (1986); A. Lubineau and E. Meyer, Tetrahedron, 44, 6065 (1988); S. Kobayashi, T. Wakabayashi, S. Nagayama, and H. Oyamada, Tetrahedron Lett., 38, 4559 (1997).
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24. As for allylation using tetraallyltin, G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; 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, T. Akiyama and J. Iwai, Tetrahedron Lett., 38, 853 (1997).
25. As for allylation using tetraallyltin, G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; 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, T. Akiyama and J. Iwai, Tetrahedron Lett., 38, 853 (1997).
26. As for allylation using tetraallyltin, G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; 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, T. Akiyama and J. Iwai, Tetrahedron Lett., 38, 853 (1997).
27. As for allylation using tetraallyltin, G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; 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, T. Akiyama and J. Iwai, Tetrahedron Lett., 38, 853 (1997).
28. As for allylation using tetraallyltin, G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; 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, T. Akiyama and J. Iwai, Tetrahedron Lett., 38, 853 (1997).
29. As for allylation using tetraallyltin, G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; 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, T. Akiyama and J. Iwai, Tetrahedron Lett., 38, 853 (1997).
30. As for allylation using tetraallyltin, G. Daude and M. Pereyre, J. Organomet. Chem., 190, 43 (1980); W. G. Peet and W. Tam, J. Chem. Soc., Chem. Commun., 1983, 853; 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, T. Akiyama and J. Iwai, Tetrahedron Lett., 38, 853 (1997).
31. 2 in organic synthesis, for example, A. J. Hubert, A. Feron, R. Warin, and P. Teyssie, Tetrahedron Lett., 1976, 1317; Y. Kobayashi, T. Taguchi, and E. Tokuno, Tetrahedron Lett., 1977, 3741; Y. Ito, T. Konoike, T. Harada, and T. Saegusa, J. Am. Chem. Soc., 99, 1487 (1977); Y. Kobayashi, T. Taguchi, T. Morikawa, E. Tokuno, and S. Sekiguchi, Chem. Pharm. Bull., 28, 262 (1980); K. Laali, R. J. Gerzina, C. M. Flajnik, C. M. Geric, and A. M. Dombroski, Helv. Chim. Acta, 70, 607 (1987); M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 1996, 871.
32. 2 in organic synthesis, for example, A. J. Hubert, A. Feron, R. Warin, and P. Teyssie, Tetrahedron Lett., 1976, 1317; Y. Kobayashi, T. Taguchi, and E. Tokuno, Tetrahedron Lett., 1977, 3741; Y. Ito, T. Konoike, T. Harada, and T. Saegusa, J. Am. Chem. Soc., 99, 1487 (1977); Y. Kobayashi, T. Taguchi, T. Morikawa, E. Tokuno, and S. Sekiguchi, Chem. Pharm. Bull., 28, 262 (1980); K. Laali, R. J. Gerzina, C. M. Flajnik, C. M. Geric, and A. M. Dombroski, Helv. Chim. Acta, 70, 607 (1987); M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 1996, 871.
33. 2 in organic synthesis, for example, A. J. Hubert, A. Feron, R. Warin, and P. Teyssie, Tetrahedron Lett., 1976, 1317; Y. Kobayashi, T. Taguchi, and E. Tokuno, Tetrahedron Lett., 1977, 3741; Y. Ito, T. Konoike, T. Harada, and T. Saegusa, J. Am. Chem. Soc., 99, 1487 (1977); Y. Kobayashi, T. Taguchi, T. Morikawa, E. Tokuno, and S. Sekiguchi, Chem. Pharm. Bull., 28, 262 (1980); K. Laali, R. J. Gerzina, C. M. Flajnik, C. M. Geric, and A. M. Dombroski, Helv. Chim. Acta, 70, 607 (1987); M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 1996, 871.
34. 2 in organic synthesis, for example, A. J. Hubert, A. Feron, R. Warin, and P. Teyssie, Tetrahedron Lett., 1976, 1317; Y. Kobayashi, T. Taguchi, and E. Tokuno, Tetrahedron Lett., 1977, 3741; Y. Ito, T. Konoike, T. Harada, and T. Saegusa, J. Am. Chem. Soc., 99, 1487 (1977); Y. Kobayashi, T. Taguchi, T. Morikawa, E. Tokuno, and S. Sekiguchi, Chem. Pharm. Bull., 28, 262 (1980); K. Laali, R. J. Gerzina, C. M. Flajnik, C. M. Geric, and A. M. Dombroski, Helv. Chim. Acta, 70, 607 (1987); M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 1996, 871.
35. 2 in organic synthesis, for example, A. J. Hubert, A. Feron, R. Warin, and P. Teyssie, Tetrahedron Lett., 1976, 1317; Y. Kobayashi, T. Taguchi, and E. Tokuno, Tetrahedron Lett., 1977, 3741; Y. Ito, T. Konoike, T. Harada, and T. Saegusa, J. Am. Chem. Soc., 99, 1487 (1977); Y. Kobayashi, T. Taguchi, T. Morikawa, E. Tokuno, and S. Sekiguchi, Chem. Pharm. Bull., 28, 262 (1980); K. Laali, R. J. Gerzina, C. M. Flajnik, C. M. Geric, and A. M. Dombroski, Helv. Chim. Acta, 70, 607 (1987); M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 1996, 871.
36. 2 in organic synthesis, for example, A. J. Hubert, A. Feron, R. Warin, and P. Teyssie, Tetrahedron Lett., 1976, 1317; Y. Kobayashi, T. Taguchi, and E. Tokuno, Tetrahedron Lett., 1977, 3741; Y. Ito, T. Konoike, T. Harada, and T. Saegusa, J. Am. Chem. Soc., 99, 1487 (1977); Y. Kobayashi, T. Taguchi, T. Morikawa, E. Tokuno, and S. Sekiguchi, Chem. Pharm. Bull., 28, 262 (1980); K. Laali, R. J. Gerzina, C. M. Flajnik, C. M. Geric, and A. M. Dombroski, Helv. Chim. Acta, 70, 607 (1987); M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 1996, 871.