Enantiomerically pure (R)- and (S)-15-hydroxy[2.2]paracyclophane-4-carbaldehyde (iso-FHPC): A novel parent compound for planar chiral ligands

European Journal of Organic Chemistry

Volumn , Issue 11, 2003, Pages 2056-2061

  Rozenberg, Valeria I ^a   Antonov, Dmitrii Yu ^a   Sergeeva, Elena V ^a   Vorontsov, Evgenii V ^a   Starikova, Zoya A ^a   Fedyanin, Ivan V ^a   Schulz, Christian ^b   Hopf, Henning ^b  

^a RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Absolute configuration determination; Cyclophanes; N,O ligands; Planar chirality; Resolution into enantiomers

Indexed keywords

15 HYDROXY[2.2]PARACYCLOPHANE 4 CARBALDEHYDE; ALDEHYDE DERIVATIVE; ALPHA METHYLBENZYLAMINE; CYCLOPHANE DERIVATIVE; LIGAND; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0037596798     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200200670     Document Type: Article

References (27)

1. [1a] V. I. Rozenberg, V. G. Kharitonov, D. Yu. Antonov, E. V. Sergeeva, A. A. Aleshkin, N. S. Ikonnikov, S. A. Orlova, Yu. N. Belokon', Angew. Chem. 1994, 106, 106-108, Angew. Chem. Int. Ed. Engl. 1994, 33, 91-93
2. [1a] V. I. Rozenberg, V. G. Kharitonov, D. Yu. Antonov, E. V. Sergeeva, A. A. Aleshkin, N. S. Ikonnikov, S. A. Orlova, Yu. N. Belokon', Angew. Chem. 1994, 106, 106-108, Angew. Chem. Int. Ed. Engl. 1994, 33, 91-93
3. [1b] H. Hopf, D. G. Barret, Liebigs Ann. 1995,449 - 451
4. [1c] D. Yu. Antonov, Yu. N. Belokon', N. S. Ikonnikov, S. A. Orlova, A. P. Pisarevsky, N. I. Raevsky, V. I. Rozenberg, E. V. Sergeeva, Yu. T. Struchkov, V. I. Tararov, E. V. Vorontsov, J. Chem. Soc., Perkin Trans. 1 1995, 1873-1879
5. [1d] D. Pamperin, C. Schulz, H. Hopf, C. Syldatk, M. Pietzsch, Eur. J. Org. Chem. 1998, 1441-1445
6. [1e] V. Rozenberg, T. Danilova, E. Sergeeva, E. Vorontsov, Z. Starikova, K. Lysenko, Yu. Belokon', Eur. J. Org. Chem. 2000, 3295-3303
7. [1f] V. I. Rozenberg, T. I. Danilova, E. V. Sergeeva, E. Vorontsov, Z. Starikova, A. Korlyukov, H. Hopf, Eur. J. Org. Chem. 2002, 468-477.
8. [2a] E. V. Sergeeva, V. I. Rozenberg, E. V. Vorontsov, T. I. Danilova, Z. A. Starikova, A. I. Yanovsky, Yu. N. Belokon', H. Hopf, Tetrahedron: Asymmetry 1996, 7, 3445-3454
9. [2b] Yu. Belokon', M. Moskalenko, N. Ikonninov, L. Yashkina, D. Antonov, E. Vorontsov, V. Rozenberg, Tetrahedron: Asymmetry 1997, 8, 3245-3250
10. [2c] V. I. Rozenberg, D. Y. Antonov, R. P. Zhuravsky, E. V. Vorontsov, V. Khrustalev, Z. A. Starikova, N. S. Ikonnikov, Yu. N. Belokon', Tetrahedron: Asymmetry 2000, 11, 2683-2693
11. [2d] N. V. Vorontsova, V. I. Rozenberg, E. V. Vorontsov, O. L. Tok, Yu. N. Bubnov, Russ. Chem. Bull. 2000, 912-919.
12. [3a] A. H. Vetter, A. Berkessel, Tetrahedron Lett. 1998, 1741-1744
13. [3b] S. Dahmen, S. Bräse, Chem. Commun. 2001, 26-27
14. [3c] S. Dahmen, S. Bräse, Org. Lett. 2001, 4119-4122
15. [3d] S. Dahmen, S. Bräse, J. Am. Chem. Soc. 2002, 124, 5940-5941.
16. X.-W. Wu, X.-L. Hou, L.-X. Dai, J. Tao, B.-X. Cao, J. Sun, Tetrahedron: Asymmetry 2001, 12, 529-532.
17. H. J. Reich, K. E. Yelm, J. Org. Chem. 1991, 56, 5672-5679.
18. H. J. Reich, D. J. Cram, J. Am. Chem. Soc. 1969, 91, 3505-3516.
19. [7a] A. Marchand, A. Maxwell, B. Mootoo, A. Pelter, A. Reid, Tetrahedron 2000, 56, 7331-7338
20. [7b] A. Pelter, B. Mootoo, A. Maxwell, A. Reid, Tetrahedron Lett. 2001, 42, 8391-8394.
21. H. Zitt, I. Dix, H. Hopf, P. G. Jones, Eur. J. Org. Chem. 2002, 2298-2307.
22. M. Psiorz, R. Schmid, Chem. Ber. 1987, 120, 1825-1828.
23. CCDC-198178 for (Rp,Sc)-8 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) +44-1223/ 336-033; E-mail: deposit@ccdc.cam.ac.uk].
24. [11a] D. J. Cram, N. L. Allinger, J. Am. Chem. Soc. 1955, 77, 6289-6294
25. [11b] H. Falk, P. Reich-Rohrwig, K. Schlögl, Tetrahedron 1970, 26, 511-527
26. [11c] J. L. Marshall, L. Hall, Tetrahedron 1981, 37, 1271-1275
27. [11d] V. I. Rozenberg, N. V. Dubrovina, E. V. Sergeeva, D. Yu. Antonov, Yu. N. Belokon', Tetrahedron: Asymmetry 1998, 9, 653-656.