Preparation and synthetic utility of 2-methylselenomethyl allyl methyl selenide. A valuable precursor to 2-silylmethylallyllithiums

Synlett

Volumn , Issue 11, 1998, Pages 1219-1222

  Krief, Alain ^a   Dumont, Willy ^a   Markó, István E ^b   Murphy, Fiona ^b   Vanherck, Jean Christophe ^b   Duval, Romain ^b   Ollevier, Thierry ^b   Abel, Ulrich ^b  

^a UNIVERSITY OF NAMUR   (Belgium)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037925648     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1915     Document Type: Article

References (27)

1. (a) Markó, I. E.; Bailey, M.; Murphy, F.; Declercq, J.-P.; Tinant, B.; Feneau-Dupont, J.; Krief, A.; Dumont, W. Synlett 1995, 123.
2. (b) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Bailey, M.; Janousek, Z.; Dolan, S. Pure Appl. Chem. 1997, 69, 565.
3. (a) Markó, I. E.; Bayston, D. J.; Mekhalfia, A.; Adams, H. Bull. Soc. Chim. Belg. 1993, 102, 655.
4. (b) Markó, I. E.; Mekhalfia, A. Tetrahedron Lett. 1992, 33, 1799.
5. (c) Markó, I. E.; Mechalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211.
6. (a) Ryter, K.; Livinghouse, T. J. Org. Chem. 1997, 62, 4842.
7. (b) Chandrasekhar, S.; Latour, S.; Wuest, J. D.; Zacharie, B. J. Org. Chem. 1983, 48, 3810.
8. (c) Keck, G E.; Palani, A. Tetrahedron Lett. 1993, 34, 3223.
9. (d) Sano, H.; Okawara, M.; Ueno, Y. Synthesis 1984, 933.
10. (a) Krief, A.; Derouane, D.; Dumont, W. Synlett 1992, 907.
11. (b) Krief, A.; Dumont, W. Tetrahedron Lett. 1997, 38, 657.
12. 2).
13. Majetich, G; Nishidie, H.; Zhang, Y. J. Chem. Soc., Perkin Trans. 1 1995, 453.
14. (a) Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683.
15. (b) Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1987, 109, 6877.
16. Ramon, D. J.; Yus, M. T. Tetrahedron 1993, 49, 10103.
17. (a) D'aniello, F.; Taddei, M. J. Org. Chem. 1992, 57, 5247.
18. (b) D'aniello, F.; Matti, D.; Taddei, M. Synlett 1993, 119.
19. (c) Knapp, S.; O'Connor, U.; Mobilio, D. Tetrahedron Lett. 1980, 21, 4557.
20. Guiles, J. W.; Meyers, A. I. J. Org. Chem. 1991, 56, 6873.
21. For selected work on polar 3-metallo-2-[heterosubstituted-methyl]propenes: (a) Gomez, C.; Ramon, D. J.; Yus, M. Tetrahedron 1993, 49, 4117.
22. (b) Alonso, F.; Lorenzo, E.; Yus, M. Tetrahedron Lett. 1998, 39, 3303.
23. (c) Vanderheide, T. A. J.; van der Baan, J. L.; Bickelhaupt, F.; Klumpp, G W. Tetrahedron Lett. 1992, 33, 475.
24. (d) van der Louw, J.; van der Baan, J. L.; Stichter, H.; Out, G J. J.; Dekanter, F. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron 1992, 48, 9877.
25. (e) van der Louw, J.; van der Baan, J. L.; Out, G J. J.; Dekanter, F. J. J.; Bickelhaupt, F.; Klumpp, G W. Tetrahedron 1992, 48, 9901.
26. For other work on 3-metallo-2-[heterosubstituted-methyl]propenes (a) Vlaar, C. P.; Klumpp, G. W. Tetrahedron Lett. 1993, 34, 4651.
27. 4). The solvents were removed under reduced pressure to afford a crude mixture which was further purified by chromatography on buffered (pH 7) silica gel (eluant: pentane/ ether: 9:1) to give the pure adducts 9. Yields are quoted in Table 2. Note: the TIPS derivative 9d is especially sensitive to traces of acid leading to unidentified decomposition products.