Enantiomer separation and absolute configuration of densely functionalized 2-oxatricyclo[4.3.1.03,8]decanes by CD spectroscopy and chemical correlation

Tetrahedron Asymmetry

Volumn 11, Issue 15, 2000, Pages 3053-3057

  Butkus, Eugenius ^a   Berg, Ulf ^b   Žilinskas, Albinas ^a   Kubilius, Rytis ^a   Stončius, Sigitas ^a  

^a VILNIUS UNIVERSITY   (Lithuania)

^b LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE;

CHEMICAL STRUCTURE; CIRCULAR DICHROISM; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; SHORT SURVEY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034637276     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00288-3     Document Type: Article

References (19)

1. Butkus, E.; Kubilius, R.; Stončius, S.; Žilinskas, A. J. Chem. Soc., Perkin Trans. 1 1999, 1431-1436.
2. Buckingham, J.; Hill, R. Atlas of Stereochemistry; Chapman and Hall: London, New York, 1986; 2nd Ed..
3. Allenmark, S. Chromatographic Enantioseparations: Methods and Applications, 2nd Ed.; Ellis Horwood: Chichester, 1991.
4. (a) Butkus, E.; Berg, U.; Stončius, A.; Rimkus, A. J. Chem. Soc., Perkin Trans. 2 1998, 2547-2551;
5. (b) Berg, U.; Butkus, E.; Frejd, T.; Bromander, S. Tetrahedron 1997, 53, 5339-5348;
6. (c) Butkus, E.; Berg, U.; Stončius, A.; Žilinskas, A. Mendeleev Commun. 1995, 96-97;
7. (d) Berg U., Butkus E. J. Chem. Res. (S) 1993, 116-117.
8. Isaksson, R.; Rochester, J. J. Org. Chem. 1985, 50, 2519-2521.
9. A Perkin Elmer Autosystem GC, equipped with split/splitless injector and flame ionization detector, was used for enantioseparation on BetaDex 120 fused silica capillary column to determine the ee of HPLC fractions.
10. Gawronski, J. In Methods of Organic Chemistry (Houben-Weyl); Helmchen, R. W.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds. Determination of absolute and relative configuration by chiroptical methods. Thieme: Stuttgart, 1996; Workbench ed. E21, Vol. 1, pp. 499-533, and references cited therein.
11. Lightner, D. A. In Circular Dichroism, Principles and Applications; Nakanishi, K.; Berova, N.; Woody R. W., Eds. The octant rule. VCH Publishers: New York, Weinheim, 1994; pp. 259-299.
12. SPARTAN Pro, Wavefunction, Inc., 18401 Von Karman, Suite 370, Irvine, California 92715.
13. Cook, M. M.; Djerassi, C. J. Am. Chem. Soc. 1973, 95, 3678-3686.
14. Snatzke, G.; Ehrig, B.; Klein, H. Tetrahedron 1969, 25, 5601-5609.
15. Bouman, T. D.; Lightner, D. A. J. Am. Chem. Soc. 1976, 98, 3145-3154.
16. Nakazaki, M.; Naemura, K. J. Org. Chem. 1977, 42, 4108-4113.
17. Hoffmann, G.; Wiartalla, R. Tetrahedron Lett. 1982, 23, 3887-3888.
18. Enantiomeric excess was determined by the rotation angle measurement and comparison with the reported data in Ref. 14.
19. 13C NMR, and mass spectra consistent with the structures presented and identical with those for the racemates (cf. Ref. 1).