Nitrogen-containing remote functionalised organolithium compounds by reductive opening of five- and six-membered heterocycles

Tetrahedron

Volumn 52, Issue 25, 1996, Pages 8545-8564

  Almena, Juan ^a   Foubelo, Francisco ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; N METHYLTETRAHYDROISOQUINOLINE; N PHENYL 3 PYRROLINE; N PHENYLISOINDOLINE; N PHENYLTETRAHYDROISOQUINOLINE; ORGANOLITHIUM COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; HYDROLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029936158     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00397-3     Document Type: Article

References (25)

1. For a review, see for instace: Comprehensive Organic Chemistry, Barton, D. H. R.; Ollia, W. D., Eds.; Pergamon Press; Oxford, 1979; Vol. 4 Part 16.
2. (a) Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400.
3. (b) For a review, see: Yus, M. Chem. Soc. Rev., submitted.
4. For the last paper on this topic from our laboratory, see: Alonso, E.; Guijarro, D.; Yus, M. Tetrahedron 1995, 51, 2699-2708.
5. For the last paper on this topic from our laboratory, see: Guijarro, A.; Yus, M. Tetrahedron 1996, 52, 1797-1810.
6. For a review, see: Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
7. For the last paper on this topic from our laboratory, see: Guijarro, A.; Ortiz, J.; Yus, M. Tetrahedron 1996, 52, 1643-1650.
8. For the last paper on this topic from our laboratory, see: Almena, J.; Foubelo, F.; Yus, M. Tetrahedron 1995, 51, 3365-3374.
9. (a) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron: Asymmetry 1995, 6, 1907-1910.
10. (b) Mudryk, K. B.; Cohen, T. J. Org. Chem. 1989, 54, 5657-5659.
11. (c) Ramón, D. J.; Yus, M. Tetrahedron 1992, 48, 3585-3588.
12. (d) Gil, J. F.; Ramón, D. J.; Yus, M. Tetrahedron 1993, 49, 9535-9546.
13. (e) Almena, J.; Foubelo, F.; Yus, M. Tetrahedron 1995, 51, 3351-3364.
14. Almena, J.; Foubelo, F.; Yus, M. J. Org. Chem. 1996, 61, 1859-1862.
15. (a) Almena, J.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1993, 34, 1649-1652.
16. (b) Almena, J.; Foubelo, F; Yus, M. J. Org. Chem. 1994, 59, 3210-3215.
17. (c) Almena, J.; Foubelo, F.; Yus, M. Tetrahedron 1994, 50, 5775-3782.
18. nLi in THF at -78°C: Ebden, M. R.; Simpkins, N. S.; Fox, D. N. A. Tetrahedron Lett. 1995, 36, 8697-8700.
19. β-Functionalised organolithium compounds are prone to β-eliminate, even at very low temperatures, giving olefins. See, for instance: Barluenga, J.; Yus, M.; Concellón, J. M.; Bernad, P. J. Org. Chem. 1983, 48, 3116-3118.
20. The reduction of conjugated double bonds with active metals, through the correspoding radical-anion intermediate, is a well-documented reaction. See, for instance: Luche, J. -L.; Cintas, P. In Active Metals, Fürstner, A., Ed.; VCH: Weinheim, 1995; pp. 146-147.
21. + signal.
22. Bobbitt, J. M.; Amundsen, L. H.; Steiner, R. I. J. Org. Chem. 1960, 25, 2230-2231.
23. Hori, M.; Kataoka, T.; Shimizu, H.; Tsutsumi, K.; Hu, Y.-Z.; Nishigiri, M. J. Chem. Soc., Perkin Trans. 1 1990, 1, 39-45.
24. Bijan Prasum Das; Basu, U. P. Indian J. Chem. 1965, 3, 268-270; Chem. Abstr. 1965, 63, 11494b.
25. Bijan Prasum Das; Basu, U. P. Indian J. Chem. 1965, 3, 268-270; Chem. Abstr. 1965, 63, 11494b.