2-Chloromethyl-3-(2-methoxyethoxy)propene: Naphthalene-catalysed lithiation and reaction towards electrophiles

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3303-3306

  Alonso, Francisco ^a   Lorenzo, Emilio ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; NAPHTHALENE DERIVATIVE; PROPYLENE;

ARTICLE; CHEMICAL REACTION; HYDROLYSIS; OXIDATION;

EID: 0032516310     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00476-6     Document Type: Article

References (28)

1. 1. Maerker, A.; Theis, M. Topics in Current Chemistry; Dewar, M. J. S.; Dunitz, J. D.; Hafner, K.; Heilbronner, E.; Ito, S.; Lehn, J.-M.; Niedenzu, K.; Raymond, K. N.; Rees, C. W; Vögtle, F.; Wittig, G., Eds.; Springer-Verlag: Berlin, 1987; Vol. 138, p 18.
2. 2. (a) Klein, J.; Medlik, A. J. Chem. Soc., Chem. Commun. 1973, 275-276,
3. (b) Bates, R. B.; Beavers, W.; Greene, M. G.; Klein, J. H. J. Am. Chem. Soc. 1974, 96, 5640-5642.
4. (c) Klein, J.; Medlik-Balan, A.; Meyer, A. Y.; Chorev, M. Tetrahedron 1976, 32, 1839-1847.
5. (d) Bahl, J. J.; Bates, R. B.; Beavers, W. A.; Mills, N. S. J. Org. Chem. 1976, 41, 1620-1622.
6. (e) Bates, R. B.; Gordon III, B.; Keller, P. C.; Rund, J. V.; Mills, N. S. J. Org. Chem. 1980, 45, 168-169.
7. 3. (a) Lochmann, L.; Pospisil, J.; Lin, D. Tetrahedron Lett. 1966, 257-262.
8. (b) Schlosser, M. J. J. Organomet. Chem . 1967, 8, 9-16.
9. (c) Bates, R. B; Beavers, W. A.; Gordon III, B.; Mills, M. S. J. Org. Chem. 1979, 44, 3800-3803.
10. 4. (a) Ramón, D. J.; Yus, M. Tetrahedron Lett. 1992, 33, 2217-2220.
11. (b) Gómez, C.; Ramón, D. J.; Yus, M. Tetrahedron 1993, 49, 4117-4126.
12. 5. (a) First account: Ramón, D. J.; Yus, M. J. Chem. Soc., Chem. Commun. 1991, 398-400.
13. (b) For a recent review, see: Yus, M. Chem. Soc. Rev. 1996, 155-161.
14. 6. (a) For a monograph, see: Blomberg, C. The Barbier Reaction and Related Processes, Springer-Verlag: Berlin, 1993.
15. (b) For a recent review, see: Alonso, F.; Yus, M. Recent Res. Devel. Org. Chem., in press.
16. 7. For leading recent references, see: (a) Majetich, G.; Nishidie, H.; Zhang, Y. J. Chem. Soc., Perkin Trans. 1 1995, 453-457.
17. (b) Kang, K. -T.; Sung, T. M.; Kim, J. K.; Kwon, Y. M. Synth. Commun. 1997, 27, 1173-1181.
18. (c) Ryter, K.; Livinghouse, T. J. Org. Chem. 1997, 62, 4842-4844.
19. (d) Clive, L. J.; Chua Paul, C.; Wang, Z. J. Org. Chem. 1997, 62, 7028-7032.
20. 8. For the last paper from our laboratory on reactions involving this process, see: Alonso, E.; Ramón, D. J.; Yus, M. Tetrahedron Lett. 1997, 38, 8903-8906.
21. 2OH, NaH) with 3-chloro-2-chloromethylpropene in DME or THF at room temperature for 1d (ca. 50% yield).
22. 10. For reviews on functionalised organolithium compounds, see: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
23. (b) Nájera, C.; Yus, M. Recent Res. Devel. Org. Chem. 1997, 1, 67-96.
24. 11. For a recent account, see: Alonso, F.; Lorenzo, E.; Yus, M. Tetrahedron Lett. 1997, 38, 2187-2190.
25. 12. For a review, see: Schuda, P. Top. Curr. Chem. 1980, 91, 75-111.
26. 13. See, for instance: Mulzer, J.; Mohr, J. -T. J. Org. Chem. 1994, 59, 1160-1165.
27. 14. See, for instance (a) Ghosh, A. K.; Kincaid, J. F.; Walters, D. E.; Chen, Y.; Chaudhuri, N. C.; Thompson, W. J.; Culberson, C.; Fitzgerald, P. M. D.; Lee, H. Y.; McKee, S. P.; Munson, P. M.; Duong, T. T.; Darke, P. L.; Zugay, J. A.; Schleif, W. A.; Axel, M. G.; Lin, J.; Huff, J. R. J. Med. Chem. 1996, 39, 3278-3290, and references cited therein.
28. (b) Chen, H.; Tan, R. X.; Liu, Z.; Zang, Y. J. Nat. Prod. 1996, 59, 668-670.