Novel strategy for the synthesis of chiral pseudo-ortho-substituted hydroxy[2.2]paracyclophane-based ligands from the resolved 4-bromo-12-hydroxy[2.2]paracyclophane as a parent compound

Tetrahedron Asymmetry

Volumn 19, Issue 2, 2008, Pages 216-222

  Zhuravsky, Roman ^a   Starikova, Zoya ^a   Vorontsov, Evgenii ^a   Rozenberg, Valeria ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

4 BROMO 12 HYDROXY[2.2]PARACYLOPHANE; ACID; BROMINE DERIVATIVE; CAMPHANIC ACID; ESTER DERIVATIVE; LIGAND; PARACYCLOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; PRIORITY JOURNAL; RACEMIC MIXTURE; SYNTHESIS;

EID: 38749126186     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.12.010     Document Type: Article

References (51)

1. See, for example:. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), Willey & Sons, New York
2. Brunel J.M. Chem. Rev. 105 (2005) 857-898
3. Baleizão C., and Garcia H. Chem. Rev. 106 (2006) 3987-4043
4. Pu L., and Yu H.-B. Chem. Rev. 101 (2001) 3987-4043 pp 757-824
5. See, for example:. Rozenberg V.I., Zhuravsky R.P., and Sergeeva E.V. Chirality 18 2 (2006) 95-102
6. Vorontsova N.V., Vorontsov E.V., Sergeeva E.V., and Rozenberg V.I. Tetrahedron Lett. 47 (2006) 2357-2360
7. Sergeeva E.V., Rozenberg V.I., Antonov D.Yu., Vorontsov E.V., Starikova Z.A., Fedyanin I.V., and Hopf H. Chem. Eur. J. 11 (2005) 6944-6961
8. Vorontsova N., Vorontsov E., Antonov D., Starikova Z., Butin K., Bräse S., Höfener S., and Rozenberg V. Adv. Synth. Catal. 347 (2005) 129-135
9. Hoffman W., and Detrick K. Synthesis 107 (1983) 107-109
10. Krohn K., Reiger H., Hopf H., Barret D., Jones P.G., and Doring D. Chem. Ber. 123 (1990) 1729-1732
11. Cipiciani A., Fringuelli F., Mancini V., Piermatti O., and Pizzo F. J. Org. Chem. 62 (1997) 3744-3747
12. Hitchcock P.B., Rowlands G.J., and Parmar R. Chem. Commun. (2005) 4219-4221
13. Rozenberg V.I., Danilova T.I., Sergeeva E.V., Vorontsov E.V., Starikova Z.A., Korlyukov A., and Hopf H. Eur. J. Org. Chem. (2002) 468-477
14. Zhang T.-Z., Dai L.-X., and Hou X.-L. Tetrahedron: Asymmetry 18 (2007) 251-259
15. Cipiciani A., Fringuelli F., Mancini V., Piermatti O., Scappini A.M., and Ruzziconi R. Tetrahedron 53 (1997) 11853-11858
16. Pamperin D., Ohse B., Hopf H., and Pietzsch M. J. Mol. Catal., B: Enzym. 5 (1998) 317-319
17. Pamperin D., Schulz C., Hopf H., Syldatk C., and Pietzsch M. Eur. J. Org, Chem. (1998) 1441-1445
18. Cipiciani A., Bellezza F., Fringuelli F., and Silvestrini M.G. Tetrahedron: Asymmetry 12 (2001) 2277-2281
19. Rozenberg V., Kharitonov V., Antonov D., Sergeeva E., Aleshkin A., Ikonnikov N., Orlova S., and Belokon' Yu. Angew. Chem., Int. Ed. Engl 33 (1994) 91-92
20. Hopf H., and Barrett D.G. Liebigs Ann. (1995) 449-451
21. Antonov D.Yu., Belokon' Yu.N., Ikonnikov N.S., Orlova S.A., Pisarevsky A.P., Raevsky N.I., Rozenberg V.I., Sergeeva E.V., Struchkov Yu.T., Tararov V.I., and Vorontsov E.V. J. Chem. Soc., Perkin Trans. 1 14 (1995) 1873-1879
22. Rozenberg V., Danilova T., Sergeeva E., Vorontsov E., Starikova Z., Lysenko K., and Belokon' Yu. Eur. J. Org. Chem. (2000) 3295-3303
23. Danilova T.I., Rozenberg V.I., Vorontsov E.V., Starikova Z.A., and Hopf H. Tetrahedron: Asymmetry 14 (2003) 1375-1383
24. Danilova T.I., Rozenberg V.I., Sergeeva E.V., Starikova Z.A., and Bräse S. Tetrahedron: Asymmetry 14 (2003) 2013-2019
25. Danilova T.I., Rozenberg V.I., Starikova Z.A., and Brase S. Tetrahedron: Asymmetry 15 (2004) 223-229
26. Vetter A.H., and Berkessel A. Tetrahedron Lett. 39 (1998) 1741-1744
27. Belokon' Yu., Moskalenko M., Ikonnikov N., Yashkina L., Antonov D., Vorontsov E., and Rozenberg V. Tetrahedron: Asymmetry 8 (1997) 3245-3250
28. Bräse S., Dahmen S., Höfener S., Lauterwasser F., Kreis M., and Ziegert R.E. Synlett 15 (2004) 2647-2669
29. Dahmen S., and Bräse S. Tetrahedron: Asymmetry 12 (2001) 2845-2850
30. Rozenberg V.I., Danilova T.I., Sergeeva E.V., Shouklov I.A., Starikova Z.A., Hopf H., and Kühlein K. Eur. J. Org. Chem. (2003) 432-440
31. Cipiciani A., Fringuelli F., Piermatti O., Pizzo F., and Ruzziconi R. J. Org. Chem. 67 (2002) 2665-2670
32. Rozenberg V.I., Antonov D.Yu., Zhuravsky R.P., Vorontsov E.V., Khrustalev V.N., Ikonnikov N.A., and Belokon' Yu.N. Tetrahedron: Asymmetry 11 (2000) 2683-2693
33. Wack H., France S., Hafez A.M., Drury III W.J., Weatherwax A., and Lectka T. J. Org. Chem. 69 (2004) 4531-4533
34. Rozenberg V.I., Antonov D.Yu., Zhuravsky R.P., Vororntsov E.V., and Starikova Z.A. Tetrahedron Lett. 44 (2003) 3801-3804
35. Cram D.J., and Day A.C. J. Org. Chem. 31 (1966) 1227-1232
36. Vorontsova N.V., Rozenberg V.I., Vorontsov E.V., Antonov D.Y., Starikova Z.A., and Bubnov Yu.N. Izv. Akad. Nauk, Ser. Khim. 8 (2002) 1369-1375 [Russ. Chem. Bull. Int. Ed. (Engl. Transl.) 2002, 8, 1483-1490]
37. Rozenberg V.I., Sergeeva E.V., and Hopf H. Cyclophanes as Templates in Stereoselective Synthesis. In: Gleiter R., and Hopf H. (Eds). Modern Cyclophane Chemistry (2004), Wiley VCH, Weinheim 435-462
38. Gibson S.E., and Knight J.D. Org. Biomol. Chem. (2003) 1256-1269
39. Braddock D.C., MacGilp I.D., and Perry B.G. J. Org. Chem. 67 (2002) 8679-8681
40. Braddock D.C., MacGilp I.D., and Perry B.G. Synlett (2003) 1121-1124
41. Braddock D.C., MacGilp I.D., and Perry B.G. Adv. Synth. Catal. 346 (2004) 1117-1130
42. Wu X.-W., Hou X.-L., Dai L.-X., Tao J., Cao B.-X., and Sun J. Tetrahedron: Asymmetry 12 (2001) 529-532
43. Focken T., Rudolph J., and Bolm C. Synthesis 3 (2005) 429-436
44. Rossen K., Pye P.J., Maliakal A., and Volante R.P. J. Org. Chem. 62 (1997) 6462-6463
45. Zhuravsky, R. P.; Rozenberg, V. I.; Antonov, D. Yu.; Vorontsov, E. V.; Starikova, Z. A.; Modern Trends in Organoelement and Polymer Chemistry, Abstract of paper, Moscow, Russia, 2004, p 166.
46. Jiang B., and Zhao X.-L. Tetrahedron: Asymmetry 15 (2004) 1141-1143
47. Gerlah H. Helv. Chim. Acta 61 (1978) 2773-2776
48. Reich H.J., and Cram D.J. J. Am. Chem. Soc. 91 (1969) 3527-3533
49. Antonov, D. Yu.; Danilova, T. I.; Vorontsov, E. V.; Starikova, Z. A.; Rozenberg, V. I. Modern Trends in Organoelement and Polymer Chemistry, Moscow, Russia, 2004, Abstract of paper, p 165.
50. Antonov, D. Y.; Rozenberg, V. I.; Danilova, T. I.; Starikova, Z. A.; Hopf, H. Eur. J. Org. Chem., in press.
51. Vorontsova N.V., Zhuravsky R.P., Sergeeva E.V., Vorontsov E.V., Starikova Z.A., and Rozenberg V.I. Izv. Akad. Nauk, Ser. Khim. 11 (2007) 2149-2155