View PDF Version
 
DOI: 10.1039/A702855E (Paper) Reference Section for: Chem. Commun., 1997, 1519-1520

Structure investigation of a dimethylaluminium derivative of ethyl rac-lactate in the solid state and solution. First evidence for stereoselective association of a dialkylaluminium O,O′-chelate complex

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

Janusz Lewiński, Janusz Zachara and Iwona Justyniak

Abstract

The reaction of AlMe3 with an equimolar amount of ethyl rac-lactate (Helac) affords rac-[Me2Al{(S*)-elac}]2; the X-ray structure shows that the adduct is formed in a highly stereoselective manner and variable-temperature 1H NMR spectra indicates that the five-coordinated complex is non-rigid in solution.

References

  1. See for example: M. Gerster, K. Schenk and P. Renaud, Angew. Chem., Int. Ed. Engl., 1996, 35, 2396 Search PubMed; T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date and M. Shibasaki, Angew. Chem., Int. Ed. Engl., 1996, 35, 104 CrossRef CAS; P. Renaud and M. Gerster, J. Am. Chem. Soc., 1995, 117, 6607 CrossRef CAS; F. H. van Steen, G. P. M. van Mier, A. L. Spek, J. Kroon and G. van Koten, J. Am. Chem. Soc., 1991, 113, 5742 CrossRef CAS; E. A. Jeffery, A. Meisters and T. Mole, J. Organomet. Chem., 1974, 74, 373 CrossRef.
  2. E. J. Vandenberg, in Catalysis in Polymer Synthesis, ACS Symp. Ser. 496, ed. E. J. Vandenberg and J. C. Salamone, Washington, DC, 1992 Search PubMed.
  3. Y. Kai, N. Yasuoka, N. Kasai and M. Kakudo, Bull. Chem. Soc. Jpn., 1972, 45, (a) 3397; (b) 3403.
  4. See for example: H. Schuman, M. Fric, B. Heymer and F. Girgsdies, J. Organomet. Chem., 1996, 512, 117 Search PubMed.
  5. (a) R. Benn, A. Rufińska, H. Lehmkuhl, E. Janssen and C. Kruger, Angew. Chem., Int. Ed. Engl., 1983, 22, 779 CrossRef; (b) D. G. Hendershot, M. Barber, R. Kumar and J. P. Oliver, Organometallics, 1991, 10, 3302 CrossRef CAS.
  6. J. Lewiński, J. Zachara, B. Mańk and S. Pasynkiewicz, J. Organomet. Chem., 1993, 454, 5 CrossRef CAS; J. Lewiński, J. Zachara, T. Kopeć and Z. Ochal, Polyhedron, 1997, 16, 1337 CrossRef CAS.
  7. Recently the synthesis and structure investigation of dialkylaluminium derivative of optically active amino alcohols have been described: M. L. Sierra, V. S. J. de Mel and J. P. Oliver, Organometallics, 1989, 8, 2486 Search PubMed; R. Kumar, M. L. Sierra and J. P. Oliver, Organometallics, 1994, 13, 4285 CrossRef CAS; D. A. Atwood, F. P. Gabai, J. Lu, M. P. Reminghton, D. Rutherford and M. P. Sibi, Organometallics, 1996, 15, 2308 CrossRef CAS.
  8. A. Haaland, Angew. Chem., Int. Ed. Engl., 1989, 28, 992 CrossRef; A. Haaland, Coordination Chemistry of Aluminum, ed. G. H. Robinson, VCH, New York, 1993, pp. 1–56 Search PubMed.
  9. The appropriate description of M–O differentiation in asymmetric bridges is really the subject of the discussion for other metal alkoxides, see for example: M. A. Matchett, M. Y. Chiang and W. E. Buhro, Inorg. Chem., 1990, 29, 360 Search PubMed.
  10. R. Benn and A. Rufińska, Angew. Chem., Int. Ed. Engl., 1986, 25, 851; R. Benn, A. Rufińska, H. Lehmkuhl and E. Janssen, J. Organomet. Chem., 1987, 333, 155 CrossRef CAS.
  11. G. M. Sheldrick, SHELXS-86, Acta Crystallogr., Sect. A, 1990, 46, 467 CrossRef.
  12. G. M. Sheldrick, SHELXL-93, University of Göttingen, 1993.
  13. H. D. Flack, Acta Crystallogr., Sect. A, 1983, 39, 876 CrossRef.