Scandium trifluoromethanesulfonate-catalyzed chemoselective allylation reactions carbonyl compounds with tetraallylgermane in aqueous media

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 853-856

  Akiyama, Takahiko ^a   Iwai, Junko ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS;

EID: 0031031831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02466-5     Document Type: Article

References (35)

1. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 1-53. Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 563-593.
2. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 1-53. Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 563-593.
3. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 1-53. Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 563-593.
4. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395-7426. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468. Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1995, 36, 6729-6732. Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 3955-3958. Yanagisawa, A.; Nakashima, H.; Ishida, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724.
5. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395-7426. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468. Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1995, 36, 6729-6732. Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 3955-3958. Yanagisawa, A.; Nakashima, H.; Ishida, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724.
6. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395-7426. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468. Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1995, 36, 6729-6732. Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 3955-3958. Yanagisawa, A.; Nakashima, H.; Ishida, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724.
7. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395-7426. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468. Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1995, 36, 6729-6732. Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 3955-3958. Yanagisawa, A.; Nakashima, H.; Ishida, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724.
8. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395-7426. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468. Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1995, 36, 6729-6732. Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 3955-3958. Yanagisawa, A.; Nakashima, H.; Ishida, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724.
9. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395-7426. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639-4640. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468. Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1995, 36, 6729-6732. Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 3955-3958. Yanagisawa, A.; Nakashima, H.; Ishida, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724.
10. For the use of tetraallyltin: a) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958-6960.
11. Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256-2257.
12. Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2342-2344. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256-2257.
13. b) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356-10357.
14. Cokley, T. M.; Marshall, R. L.; McClusky, A.; Young, J. J. Tetrahedron Lett. 1996, 39, 1905-1908.
15. Majetich, G. In Organic Synthesis, Theory and Applications.; Hudlicky Ed.; JAI Press, Inc.: Greenwich, CT, 1989; pp. 173-241. Fleming, I.; Dunogues, J.; Smithers, R. Org. React. (N.Y.) 1989, 37, 57-575.
16. Majetich, G. In Organic Synthesis, Theory and Applications.; Hudlicky Ed.; JAI Press, Inc.: Greenwich, CT, 1989; pp. 173-241. Fleming, I.; Dunogues, J.; Smithers, R. Org. React. (N.Y.) 1989, 37, 57-575.
17. For the use of allylgermane as an allylmetal: Sano, H.; Miyazaki, Y.; Okawara, M.; Ueno, Y. Synthesis 1986, 776-777. Yamamoto, Y.; Matsuya, S.; Yamada, J. J. Org. Chem. 1990, 55, 3118-3128. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121. Yamamoto, Y.; Okano, H.; Yamada, J. Tetrahedron Lett. 1991, 32, 4749-4752. Denmark, S. E.; Almstead, N. B. J. Org. Chem. 1991, 56, 6485-6487. Hashimoto, Y.; Kagoshima, H.; Saigo, K. Tetrahedron Lett. 1994, 35, 4805-4808.
18. For the use of allylgermane as an allylmetal: Sano, H.; Miyazaki, Y.; Okawara, M.; Ueno, Y. Synthesis 1986, 776-777. Yamamoto, Y.; Matsuya, S.; Yamada, J. J. Org. Chem. 1990, 55, 3118-3128. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121. Yamamoto, Y.; Okano, H.; Yamada, J. Tetrahedron Lett. 1991, 32, 4749-4752. Denmark, S. E.; Almstead, N. B. J. Org. Chem. 1991, 56, 6485-6487. Hashimoto, Y.; Kagoshima, H.; Saigo, K. Tetrahedron Lett. 1994, 35, 4805-4808.
19. For the use of allylgermane as an allylmetal: Sano, H.; Miyazaki, Y.; Okawara, M.; Ueno, Y. Synthesis 1986, 776-777. Yamamoto, Y.; Matsuya, S.; Yamada, J. J. Org. Chem. 1990, 55, 3118-3128. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121. Yamamoto, Y.; Okano, H.; Yamada, J. Tetrahedron Lett. 1991, 32, 4749-4752. Denmark, S. E.; Almstead, N. B. J. Org. Chem. 1991, 56, 6485-6487. Hashimoto, Y.; Kagoshima, H.; Saigo, K. Tetrahedron Lett. 1994, 35, 4805-4808.
20. For the use of allylgermane as an allylmetal: Sano, H.; Miyazaki, Y.; Okawara, M.; Ueno, Y. Synthesis 1986, 776-777. Yamamoto, Y.; Matsuya, S.; Yamada, J. J. Org. Chem. 1990, 55, 3118-3128. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121. Yamamoto, Y.; Okano, H.; Yamada, J. Tetrahedron Lett. 1991, 32, 4749-4752. Denmark, S. E.; Almstead, N. B. J. Org. Chem. 1991, 56, 6485-6487. Hashimoto, Y.; Kagoshima, H.; Saigo, K. Tetrahedron Lett. 1994, 35, 4805-4808.
21. For the use of allylgermane as an allylmetal: Sano, H.; Miyazaki, Y.; Okawara, M.; Ueno, Y. Synthesis 1986, 776-777. Yamamoto, Y.; Matsuya, S.; Yamada, J. J. Org. Chem. 1990, 55, 3118-3128. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121. Yamamoto, Y.; Okano, H.; Yamada, J. Tetrahedron Lett. 1991, 32, 4749-4752. Denmark, S. E.; Almstead, N. B. J. Org. Chem. 1991, 56, 6485-6487. Hashimoto, Y.; Kagoshima, H.; Saigo, K. Tetrahedron Lett. 1994, 35, 4805-4808.
22. For the use of allylgermane as an allylmetal: Sano, H.; Miyazaki, Y.; Okawara, M.; Ueno, Y. Synthesis 1986, 776-777. Yamamoto, Y.; Matsuya, S.; Yamada, J. J. Org. Chem. 1990, 55, 3118-3128. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116-6121. Yamamoto, Y.; Okano, H.; Yamada, J. Tetrahedron Lett. 1991, 32, 4749-4752. Denmark, S. E.; Almstead, N. B. J. Org. Chem. 1991, 56, 6485-6487. Hashimoto, Y.; Kagoshima, H.; Saigo, K. Tetrahedron Lett. 1994, 35, 4805-4808.
23. For organogermanium compounds in organic synthesis: Yokoyama, Y.; Mochida, K. Synlett 1996, 445-446. See also references cited therein.
24. Barnes, J. M.; Magos, L. Organometal. Chem. Rev. 1968, 3, 137-150.
25. Reissig, H. -U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; pp. 71-76. Li, C.-J. Chem. Rev. 1993, 93, 2023-2035.
26. Reissig, H. -U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; pp. 71-76. Li, C.-J. Chem. Rev. 1993, 93, 2023-2035.
27. O'Brien, S.; Fishwick, M.; Mcdermott, B.; Wallbridge, M. G. H.; Wright, G. A. Inorg. Synth. 1971, 13, 73. Tetraallylgermane is fairly stable in acidic aqueous media.
28. Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474.
29. 3 were found to be less effective.
30. 3 in nitromethane: Aggarwal, V. K.; Vennall, G. P. Tetrahedron Lett. 1996, 37, 3745-3746.
31. 2, hexane: ethyl acetate = 6 : 1, v/v) gave 1 (37.2 mg) in 94% yield.
32. 3a
33. Okude,Y.; Hirano, S.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179-3181. Reetz, M. T.; Wendderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262.
34. Okude,Y.; Hirano, S.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179-3181. Reetz, M. T.; Wendderoth, B. Tetrahedron Lett. 1982, 23, 5259-5262.
35. Effect of water on lanthanide(III)-triflate promoted reactions is discussed: Kobayashi, S. Synlett 1994, 689-701.