Synthesis of chiral calix[n]arenes. Part 2: Synthesis of new chiral calix[n]arenes based on (p-hydroxy-phenyl)-menthone

Tetrahedron Asymmetry

Volumn 10, Issue 1, 1999, Pages 177-182

  Soi, Antonio ^a,b   Pfeiffer, Jens ^a   Jauch, Johann ^a,c   Schurig, Volker ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^c TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0033556504     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00483-2     Document Type: Article

References (17)

1. (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
2. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds, Böhmer, V.; Vicens, J., Eds; Kluwer: Dordrecht, 1991.
3. (c) Shinkai, S. Tetrahedron 1993, 49, 8933-8968.
4. (d) Böhmer, V.; Kraft, D.; Tabatabai, M. J. Ind. Phenom. 1994, 19, 17-39.
5. (e) Böhmer, V. Angew. Chem. 1995, 107, 785-818.
6. (f) Böhmer, V. Angew. Chem., Int. Ed. Engt. 1995, 34, 713-745.
7. Jauch, J.; Schurig, V. Tetrahedron: Asymmetry 1997, 8, 169-172.
8. (a) Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908-6909.
9. (b) Buschmann, H.; Scharf, H. D. Synthesis 1988, 827-830.
10. (c) Ort, O. Org. Synth. 1987, 65, 203-213.
11. Beyermann, H. C.; Bontekoe, J. S. Recl. Trav. Chim. Pays-Bas. 1962, 81, 691-698.
12. Grosenick, H.; Schurig, V. J. Chromatogr. 1997, A, 761, 181-193.
13. Kinetic studies starting from a mixture of 4 and 5 (20:80) showed that after 1 h, the epimeric ratio of the products 6 and epi-6 has equilibrated to 78:22. 6 and epi-6 were separated by flash chromatography with 30% diethyl ether in n-hexane. (illustration presented)
14. (a) Gutsche, C. D.; Jqbal, M. Org. Synth. 1989, 68, 234-237.
15. (b) Gutsche, C. D.; Dhawan, B.; Leonis, M.; Tewart, D. Org. Synth. 1989, 68, 238-242.
16. (c) Munch, J. H.; Gutsche, C. D. Org. Synth. 1989, 68, 243-246.
17. If a solid precipitate forms, the mixture has to be warmed until the precipitate dissolves again. Otherwise neutralization is incomplete which results in decreased yields since the tert-butyl group is partially removed under these acidic conditions.