Chiral β-lithio enol ethers: Synthesis and properties

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7255-7258

  Godebout, Virginie ^a   Lecomte, Sandrine ^a   Levasseur, Frederic ^a   Duhamel, Lucette ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030607158     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01662-0     Document Type: Article

References (23)

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3. c) Duhamel, L.; Tombret, F.; J. Organomet. Chem. 1985, 280, 1-16.
4. (2) This methodology gives access to t-butoxyacetylene via 2-bromo-1-t-butoxyacetylene : Pericas, M. A.; Serratosa, F.; Valenti, E.; Tetrahedron 1987, 43, 2311-2316.
5. 1c and Duhamel, L.; Tombret, F.; Poirier, J.M.; Organic Preparations and Procedures Int. 1985, 17, 99-105.
6. 1c and Duhamel, L.; Tombret, F.; Poirier, J.M.; Organic Preparations and Procedures Int. 1985, 17, 99-105.
7. 1b, c, 3
8. (5) a) Greene, A. E.; Charbonnier, F.; Tetrahedron Lett. 1985, 26, 5525-5528. Greene, A. E.; Charbonnier, F.; Luche, M. J.; Moyano, A.; J. Am. Chem. Soc. 1987, 109, 4752-4753.
9. (5) a) Greene, A. E.; Charbonnier, F.; Tetrahedron Lett. 1985, 26, 5525-5528. Greene, A. E.; Charbonnier, F.; Luche, M. J.; Moyano, A.; J. Am. Chem. Soc. 1987, 109, 4752-4753.
10. b) De Azevedo, M. B.; Murta, M. M.; Greene, A. E.; J. Org. Chem. 1992, 57, 4567-4569.
11. c) Ganz, I.; Kunz, H.; Synthesis 1994, 1353-1358.
12. (6) Boa, A. N.; Dawkins, D. A.; Hergueta, A. R.; Perkins, P. R.; J. Chem. Soc. Perkin Trans I 1994, 953-960.
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14. b) Choudhury, A.; Franck, R. W.; Gupta, R. B.; Tetrahedron Lett. 1989, 30, 4921-4924.
15. c) Backvall, J. E.; Rise, F.; Tetrahedron Lett 1989, 30, 5347-5348.
16. d) Dujardin, G.; Molato, S.; Brown, E.; Tetrahedron : Asymmetry 1993, 4, 193-196
17. (8) Faunce, J.A.; Grisso, B.A.; Mackenzie, B.; J. Am. Chem.Soc. 1991, 113, 3418-3426.
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22. (11) See : Dujardin, G.; Rossignol, S.; Brown, E.; Tetrahedron Lett. 1995, 36, 1653-1656, for the preparation of chiral 2-alkoxy propenes isomers of 5a and 5b.
23. 4) and concentrated to provide enol ether 5. Enol ethers 6-7 : Lithium bromide (4.78 mmol, 0.42g) was introduced in a flask and dried by heating under vacuum. THF (2.5 ml) was then added. The solution was cooled down to -70°C before adding t-butyllithium (1.54M in pentane, 2.20 mmol, 1.43 ml), then bromo enol ether 1 (0.96 mmol) in THF (1.35 ml). After stirring for 90 minutes at -70°C, alkyliodide (1.93 mmol) was added and the mixture worked up as in the case of enol ethers 5.