Preparation of γ-heterosubstituted allylindium and diindium reagents and their reactions with carbonyl compounds

Journal of Organic Chemistry

Volumn 64, Issue 1, 1999, Pages 172-177

  Hirashita, Tsunehisa ^a   Kamei, Toshiya ^a   Horie, Tomoaki ^a   Yamamura, Hatsuo ^a   Kawai, Masao ^a   Araki, Shuki ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ALLYLINDIUM; GAMMA ALKOXYALLYLLITHIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033534707     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9816111     Document Type: Article

References (31)

1. Cintas, P. Synlett 1995, 1087-1096, and references therein.
2. Araki, S.; Hirashita, T.; Shimizu, K.; Butsugan, Y. Tetrahedron 1996, 52, 2803-2816.
3. Araki, S.; Hirashita, T.; Shimizu, H.; Yamamura, H.; Kawai, M. Tetrahedron Lett. 1996, 37, 8417-8420.
4. Chen, D.-L.; Li, C.-J. Tetrahedron Lett. 1996, 37, 295-298.
5. (a) Isacc, M. B.; Chan, T.-H. Tetrahedron Lett. 1995, 36, 8957-8960.
6. (b) Kirihara, M.; Takuwa, T.; Takizawa, S.; Momose, T. Tetrahedron Lett. 1997, 38, 2853-2854.
7. Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831-1833.
8. Labaudinère, L.; Hanaizi, J.; Normant, J.-F. J. Org. Chem. 1992, 57, 6903-6908.
9. For the reaction of γ-alkoxyallymetal reagents with carbonyl compounds, see: (Sn) (a) Koreeda, M.; Tanaka, Y. Tetrahedron Lett. 1987, 28, 143-146.
10. (b) Marshall, J. A.; Luke, G. P. J. Org. Chem. 1991, 56, 483-485. (Al)
11. (c) Koreeda, M.; Tanaka, Y. J. Chem. Soc., Chem. Commun. 1982, 845-847.
12. (d) Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096-1104. (B)
13. (e) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535-1538. (Fe)
14. (f) Jiang, S.; Agoston, G. E.; Chen, T.; Cabal, M.-P.; Turos, E. Organometallics 1995, 14, 4697-4709.
15. (a) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920-1921.
16. (b) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 105-108.
17. (c) Marshall, J. A.; Garofalo, A. W. J. Org. Chem. 1996, 61, 8732-8738.
18. Paquette, L. A.; Bennett, G. D.; Issac, M. B.; Chhatriwalla, A. J. Org. Chem. 1998, 63, 1836-1845, and references therein.
19. For allylic gemmai dimetallic species, see: (a) Marek, I.; Normant, J.-F. Chem. Rev. 1996, 96, 3241-3267.
20. (b) Madec, D.; Férézou, J.-P. Tetrahedron Lett. 1997, 38, 6657-6660.
21. Beruben, D.; Marek, I.; Normant, J.-F. Tetrahedron 1996, 52, 7235-7250.
22. Schlosser, M.; Strunk, S. Tetrahedron 1989, 45, 2649-2664.
23. Auge, J.; Davis, S. Tetrahedron Lett. 1983, 24, 4009-4012.
24. Osuka, A.; Suzuki, H. Tetrahedron Lett. 1983, 24, 5109-5112.
25. Araki, S.; Ito, K., Butsugan, Y. Appl. Organomet. Chem. 1988, 475-478.
26. Furuta, K.; Ikeda, Y.; Meguriya, N.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2781-2790.
27. Newcomb, M.; Le Tadic, M.-H.; Chesteny, D.-L.; Roberts, E. S.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 12085-12091.
28. Al'bitskaya, V. M.; Petrov, A. A.; Blyakman, E. M. Zh. Obshch. Khim. 1961, 31, 2166-2171; Chem. Abstr. 1962, 56, 2363f.
29. Al'bitskaya, V. M.; Petrov, A. A.; Blyakman, E. M. Zh. Obshch. Khim. 1961, 31, 2166-2171; Chem. Abstr. 1962, 56, 2363f.
30. Tsai, D. J. S.; Matteson, D. Tetrahedron Lett. 1981, 22, 2751-2752.
31. Christie, S. D. R.; Cosset, C.; Hamilton, D. R.; Kerr, W. J.; O'Callaghan, M. J. Chem. Soc., Chem. Commun. 1995, 2051-2052.