Asymmetric addition of Davies's chiral lithium amide to prochiral vinyl phosphine oxides

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1637-1640

  Bartels, Björn ^a   Martín, Concepcion Gonzalez ^a   Nelson, Adam ^a   Russell, Matthew G ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; LITHIUM DERIVATIVE; OXIDE; PHOSPHINE; VINYL DERIVATIVE;

ARTICLE; DIASTEREOISOMER;

EID: 0032546191     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10860-7     Document Type: Article

References (31)

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2. 2. For example: Bunnage, M. E.; Burke, A. J.; Davies, S. G.; Goodwin, C. J. Tetrahedron: Asymmetry, 1995, 6, 165-176; Bunnage, M. E.; Davies, S. G.; Goodwin, C. J.; Ichihara, O. Tetrahedron, 1994, 50, 3975-3986.
3. 2. For example: Bunnage, M. E.; Burke, A. J.; Davies, S. G.; Goodwin, C. J. Tetrahedron: Asymmetry, 1995, 6, 165-176; Bunnage, M. E.; Davies, S. G.; Goodwin, C. J.; Ichihara, O. Tetrahedron, 1994, 50, 3975-3986.
4. 3. Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 ,1994, 2385-2391.
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6. 5. Davies, S. G.; Hedgecock, C. J. R.; McKenna, J. M. Tetrahedron: Asymmetry, 1995, 6, 2507-2510; Davies, S. G.; Hedgecock, C. J. R.; McKenna, J. M. Tetrahedron: Asymmetry, 1995, 6, 827-830.
7. 5. Davies, S. G.; Hedgecock, C. J. R.; McKenna, J. M. Tetrahedron: Asymmetry, 1995, 6, 2507-2510; Davies, S. G.; Hedgecock, C. J. R.; McKenna, J. M. Tetrahedron: Asymmetry, 1995, 6, 827-830.
8. 6. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry, 1996, 7, 1595-1598.
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14. 12. Armstrong, S. K.; Warren, S. unpublished results.
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19. 15. Attempted purification of the crude reaction mixture on silica gel led to desilylation of 11, but the β-amino phosphine oxides 12 were not separable from the α-silyl phosphine oxides 10.
20. 4), filtered and evaporated under reduced pressure to give a crude product. Purification by flash chromatography, eluting with EtOAc-hexane (1:1) gave the β-amino phosphine oxides as colourless oils.
21. 17. Lithium amides react slowly with trimethylsilyl chloride at -78 °C in THF: Lipschutz, B. H.; Wood, M. R.; Lindsley, C. W. Tetrahedron Lett., 1995, 36, 4385-4388.
22. 18. For another β-elimination of a β-amino organolithium compound, see: Barluenga, J.; Sanz, R.; Fañanás, F. J. Tetrahedron Lett., 1997, 38, 2763-2766.
23. 19. For other examples of selective hydrogenolyses, see reference 2.
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26. 21 would have been unreliable with our compiounds. (equation presented)
27. 23. Kreuger, C.; Trost, B. M. personal communication.
28. 24. Satisfactory analytical data was obtained for all new compounds.
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31. 26. Davies, I. W.; Gallagher, T.; Lamont, R. B.; Scopes, D. I. C. J. Chem. Soc., Chem. Commun., 1992, 335-337.