Synthesis and novel structure of the first crystallographically characterised chiral α-amino lithium alkoxide

(Note: The full text of this document is currently only available in the PDF Version )

John E. Davies, Paul R. Raithby, Ronald Snaith and Andrew E. H. Wheatley


Abstract

Lithium N,N,N′-trimethylethylenediamide, LiN(Me)(CH2)2NMe2, reacts with o-anisaldehyde, o-MeOC6H4CHO, to afford a chiral α-amino lithium alkoxide 1, which in the solid state is a racemic tetramer with an ‘open’ pseudo-cubane core; the extent to which the N,N,N′-trimethylethylenediamido moieties internally solvate the Li centres varies with the chirality of the protected aldehyde groups.


References

  1. H. W. Gschwend and H. R. Rodriguez, Org. React., 1979, 26, 1 CAS; I. Omae, Chem. Rev., 1979, 79, 287 CrossRef CAS; P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306 CrossRef CAS; N. S. Narasimhan and R. S. Mali, Synthesis, 1983, 957 CrossRef CAS; N. S. Narasimhan and R. S. Mali, Top. Curr. Chem., 1987, 138, 63 CAS; V. Snieckus, Chem. Rev., 1990, 90, 879 CrossRef CAS.
  2. D. L. Comins and J. D. Brown, J. Org. Chem., 1984, 49, 1078 CrossRef CAS and references 2–10 therein.
  3. D. L. Comins and J. D. Brown, Tetrahedron Lett., 1981, 22, 4213 CrossRef CAS; D. L. Comins, J. D. Brown and N. B. Mantlo, Tetrahedron Lett., 1982, 23, 3979 CrossRef CAS; D. L. Comins and J. D. Brown, J. Org. Chem., 1989, 54, 3730 CrossRef CAS.
  4. D. L. Comins and M. O. Killpack, J. Org. Chem., 1987, 52, 104 CrossRef CAS.
  5. (a) E. M. Arnett, M. A. Nichols and A. T. McPhail, J. Am. Chem. Soc., 1990, 112, 7059 CrossRef CAS; (b) M. A. Nichols, A. T. McPhail and E. M. Arnett, J. Am. Chem. Soc., 1991, 113, 6222 CrossRef CAS; (c) G. Hilmersson and Ö. Davidsson, J. Organomet. Chem., 1995, 489, 175 CrossRef CAS; G. Hilmersson and Ö. Davidsson, Organometallics, 1995, 14, 912 CrossRef CAS; (d) G. Hilmersson and Ö. Davidsson, J. Org. Chem., 1995, 60, 7660 CrossRef CAS; (e) H. J. Reich and K. J. Kulicke, J. Am. Chem. Soc., 1995, 117, 6621 CrossRef CAS; (f) J. M. Saá, G. Martorelli and A. Frontera, J. Org. Chem., 1996, 61, 5194 CrossRef CAS; (g) K. Sugasawa, M. Shindo, H. Noguchi and K. Koga, Tetrahedron Lett., 1996, 37, 7377 CrossRef CAS.
  6. A. Tatsukawa, K. Kawatake, S. Kanemasa and J. M. Rudzinski, J. Chem. Soc., Perkin Trans. 2, 1994, 2525 RSC; R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673 CAS; L. M. Pratt and I. M. Khan, Tetrahedron Lett., 1995, 6, 2165 CrossRef CAS; G. Fraenkel, S. Subramanian and A. Chow, J. Am. Chem. Soc., 1995, 117, 6300 CrossRef CAS.
  7. T. Kottke and D. Stalke, J. Appl. Crystallogr., 1993, 26, 615 CrossRef.
  8. G. M. Sheldrick, Acta Crystallogr., Sect. C, 1990, A46, 467 CAS.
  9. G. M. Sheldrick, SHELXL-93, Program for Crystal Structure Refinement, University of Göttingen, 1993.
  10. O. Graalmann, U. Klingebiel, W. Clegg, M. Haase and G. M. Sheldrick, Angew. Chem., 1984, 96, 904 CAS; Angew. Chem., Int. Edn. Engl., 1984, 23, 891 Search PubMed; J. T. B. H. Jastrzebski, G. van Koten, M. J. N. Christophersen and C. H. Stam, J. Organomet. Chem., 1985, 292, 319 Search PubMed; T. Maetzke and D. Seebach, Organometallics, 1990, 9, 3032 CrossRef CAS; S. C. Ball, I. Cragg-Hine, M. G. Davidson, R. P. Davies, M. I. Lopez-Solera, P. R. Raithby, D. Reed, R. Snaith and E. M. Vogl, J. Chem. Soc., Chem. Commun., 1995, 2147 CrossRef CAS.
  11. G. W. Klumpp, Rec. Trav. Chim. Pays-Bas, 1986, 105, 1 Search PubMed.
  12. M. Pink, G. Zahn and J. Sieler, Z. Allorg. Allg. Chem., 1994, 620, 749 Search PubMed.
  13. A. J. Edwards, M. A. Paver, P. R. Raithby, C. A. Russell and D. S. Wright, J. Chem. Soc., Dalton Trans., 1993, 3265 RSC.
  14. A. Bax, R. H. Griffey and B. L. Hawkins, J. Magn. Reson., 1983, 55, 301 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.