EPC-synthesis of functionalised amides via chiral β-nitrogenated organolithium compounds

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2911-2922

  Foubelo, Francisco ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; AMIDE; CYCLOALKANOL DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; TECHNIQUE;

EID: 0030271750     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00382-5     Document Type: Article

References (43)

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6. n reagents, following the Seebach nomenclature: Seebach, D. Angew. Chem. Int. Ed. Eng. 1979, 18, 239-258.
7. 7. The β-elimination process has been shown to be useful for the regioselective non-stereoselective preparation of olefins. For the first report on this methodology, see: Barluenga, J.; Yus, M.; Bernad, P. J. Chem. Soc., Chem. Commun. 1978, 847-847.
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9. 9. See, for instance: Barluenga, J.; Fañanás, F. J.; Villamaña, J.; Yus, M. J. Chem. Soc., Perkin Trans. I 1984, 2685-2692 and previous papers on this topic from our group cited therein.
10. 10. For the first paper on this topic, see: Barluenga, J.; Foubelo, F.; Fañanás, F. J.; Yus, M. Tetrahedron Lett. 1988, 29, 2859-2860.
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33. 11 led to decomposition of the starting material, so this methodology can not be applied in this process. See also, Barluenga, J.; Monserrat, J. M.; Flórez, J. J. Org. Chem. 1993, 55, 5976-5980.
34. 17. We found that it is not necessary to stir the reaction mixture for 8 h in order to complete the lithiation step; see references 10 and 16.
35. 18. The optical purity of the obtained compounds 3, 6, 9, 12, 15 and 18 is related to the correponding starting materials, since no racemisation has ever been observed for this type of systems. (a) See references 13g and 13i.
36. (b) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron: Asymmetry 1995, 6, 2081-2092.
37. 19. The same results were obtained using chiral β-oxygenated organolithium compounds; see reference 13g and 18b. This behaviour should be attributed to the high reactivity of intermediates of the type II, even at very low temperatures.
38. 20. Dianionic intermediates 2, 5, 8, 11, 14 and 17 are very sensitive to the temperature and suffer decomposition (β-elimination or proton abstraction) during their reaction with gaseous carbon dioxide.
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