Enantiomerization barriers by dynamic HPLC. Stationary phase effects

Tetrahedron Asymmetry

Volumn 8, Issue 12, 1997, Pages 2069-2073

  Gasparrini, Francesco ^a   Misiti, Domenico ^a   Pierini, Marco ^a   Villani, Claudio ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; CONFORMATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 0031000294     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00216-4     Document Type: Article

References (23)

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3. Casarini, D.; Cirilli, M.; Gasparrini, F.; Gavuzzo, E.; Lunazzi, L.; Villani, C. J. Org. Chem. 1995, 60, 97.
4. Villani, C.; Pirkle, W. H. Tetrahedron: Asymmetry 1995, 6, 27.
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16. b) Pirkle, W. H.; Welch, C. J.; Zych, A. J. J. Chromatogr. 1993, 648, 101;
17. c) Bowles, P.; Clayden, J.; Tomkinson, M. Tetrahedron Lett. 1995, 36, 9219.
18. s for 1-4; we make no attempt to interpret energy barriers in terms of sequential or correlated Ar-CO rotation (HPLC visible on a CSP) and CO-N rotation (HPLC invisible for 1-4).
19. Lefèvre, F.; Burgemeister, T.; Mannschreck, A. Tetrahedron Lett. 1977, 1125.
20. Gasparrini, F.; Misiti, D.; Pierini, M.; Villani, C. J. Chromatogr. A 1996, 724, 79.
21. The configurational description of the commercial (S,S)-Whelk-O1 phase (used in this study) has been revised and corrected to (3R,45); see: Pirkle, W. H.; Brice, L. J.; Widlanski, T. S.; Roestamadji, J. Tetrahedron: Asymmetry 1996, 7, 2173.
22. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds John Wiley and Sons, New York, 1994, p. 426.
23. Jung, M. QCPE Bull. 1992, 12, 52.