Synthesis of and asymmetric induction by chiral polycyclic thiazolium salts

Tetrahedron Letters

Volumn 38, Issue 20, 1997, Pages 3615-3618

  Gerhard, A Ulrich ^a   Leeper, Finian J ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIN; THIAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0030920183     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00682-5     Document Type: Article

References (9)

1. Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, preceding paper.
2. Girard, C.; Conia, J. M. Tetrahedron Lett. 1974, 15, 3327-3328.
3. Ali, S. M.; Matsuda, Y.; Tanimoto, S. Synthesis 1988, 805-806.
4. Shaw, K. N. F.; Nolan, C. J. Org. Chem. 1957, 22, 1668-1670.
5. The crystal structures were solved by Dr. J. E. Davies (Cambridge) using the program SHELXL93: Sheldrick, G. M., SHELXL93, University of Göttingen, 1993. The absolute configurations were established according to the procedure of Flack, H. D. Acta Cryst. A 1983, 39, 876-881. For 8a, X = 0.01(2). For 7b, X = -0.02(4); in this crystal structure two orientations of the anthracene moiety were observed, the major one (59%) is shown in bold in Fig. 1(b). The data have been deposited with the Cambridge Crystallographic Data Centre, refcodes 100158 for 8a and 100160 for 7b.
6. Graue, C.; Klingenberg, M. Biochim. Biophys. Acta 1979, 546, 539-550.
7. Jones, B. J. Chem. Soc. 1933, 788-796.
8. Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221.
9. Triazolium ions catalyse the benzoin condensation in the same way as do thiazolium ions.