Stereoselective synthesis of cis-4,7-disubstituted 4,7-dihydroxy-4,7-dihydro[2.2] paracyclophanes

Russian Chemical Bulletin

Volumn 51, Issue 8, 2002, Pages 1483-1490

  Vorontsova, N V ^a   Rozenberg, V I ^a   Vorontsov, E V ^a   Antonov, D Yu ^a   Starikova, Z A ^a   Bubnov, Yu N ^a  

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

Author keywords

2.2 paracyclophanes; Allylboration; Nucleophilic addition; Organoboron compounds; Organolithium compounds; Quinones; Stereoselectivity; X ray diffraction analysis

Indexed keywords

4,7 DIALLYL 4,7 DIHYDROXY 4,7 DIHYDRO[2.2]PARACYCLOPHANE; 4,7 DIBUTYL 4,7 DIHYDROXY 4,7 DIHYDRO[2.2]PARACYCLOPHANE; 4,7 DIHYDROXY 4,7 DIHYDRO 4,7 DIMETHYL[2.2]PARACYCLOPHANE; 4,7 DIHYDROXY 4,7 DIHYDRO 4,7 DIPHENYL[2.2]PARACYCLOPHANE; [2.2]PARACYCLOPHANE 4,7 QUINONE; BORANE DERIVATIVE; BUTYLLITHIUM; LITHIUM DERIVATIVE; METHYLLITHIUM; PARACYCLOPHANE DERIVATIVE; PHENYLLITHIUM; QUINONE DERIVATIVE; TRIALLYLBORANE; UNCLASSIFIED DRUG;

ARTICLE; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0036432632     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1020915107378     Document Type: Article

References (29)

1. R. Yanada, M. Higashikava, Y. Miwa, T. Taga, and F. YonEda, Tetrahedron Asymmetry, 1992, 3, 1387.
2. V. Rozenberg, V. Kharitonov, D. Antonov, E. Sergeeva, A. Aleshkin, N. Ikonnikov, S. Orlova, and Yu. Belokon', Angew. Chem., Int. Ed. Engl., 1994, 33, 91.
3. A. Pelter, R. A. N. C. Crump, and H. Kidwell, Tetrahedron Lett., 1996, 37, 1273.
4. Yu. Belokon', M. Moskalenko, N. Ikonninov, L. Yashkina, D. Antonov, E. Vorontsov, and V. Rozenberg, Tetrahedron Asymmetry, 1997, 8, 3245.
5. P. J. Pye, K. Rossen, R. A. Reamer, N. N. Tsou, R. P. Volante, and P. J. Reider, J. Am. Chem. Soc., 1997, 119, 6207.
6. D. J. Cram and F. L. Harris, Jr., J. Am. Chem. Soc., 1967, 89, 4642.
7. A. Pelter, H. Kidwell, and R. A. N. C. Crump, J. Chem. Soc., Perkin Trans. 1, 1997, 3137.
8. H. J. Reich and K. E. Yelm, J. Org. Chem., 1991, 56, 5672.
9. E. V. Sergeeva, V. I. Rozenberg, E. V. Vorontsov, T. I. Danilova, Z. A. Starikova, A. I. Yanovsky, and Yu. N. Belokon', Tetrahedron Asymmetry, 1996, 7, 3445.
10. N. V. Vorontsova, V. I. Rozenberg, E. V. Vorontsov, O. L. Tok, and Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 2000, 914 [Russ. Chem. Bull., Int. Ed., 2000, 49, 912].
11. N. V. Vorontsova, V. I. Rozenberg, E. V. Vorontsov, O. L. Tok, and Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 2000, 914 [Russ. Chem. Bull., Int. Ed., 2000, 49, 912].
12. D. J. Cram and H. P. Fisher, J. Org. Chem., 1965, 30, 1815.
13. D. J. Cram and A. C. Day, J. Org. Chem., 1966, 31, 1227.
14. N. V. Vorontsova, V. I. Rozenberg, E. V. Vorontsov, D. Yu. Antonov, and Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 2000, 568 [Russ. Chem. Bull., Int. Ed., 2000, 49, 572].
15. N. V. Vorontsova, V. I. Rozenberg, E. V. Vorontsov, D. Yu. Antonov, and Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 2000, 568 [Russ. Chem. Bull., Int. Ed., 2000, 49, 572].
16. B. M. Mikhailov, G. S. Ter-Sarkisyan, and N. A. Nikolaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1968, 541 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1968, 547 (Engl. Transl.)].
17. B. M. Mikhailov, G. S. Ter-Sarkisyan, and N. A. Nikolaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1968, 541 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1968, 547 (Engl. Transl.)].
18. G. S. Ter-Sarkisyan, N. A. Nikolaeva, V. G. Kiselev, and B. M. Mikhailov, Zh. Obshch. Khim., 1971, 41, 152 [J. Gen. Chem. USSR, 1971, 41 (Engl. Transl.)].
19. G. S. Ter-Sarkisyan, N. A. Nikolaeva, V. G. Kiselev, and B. M. Mikhailov, Zh. Obshch. Khim., 1971, 41, 152 [J. Gen. Chem. USSR, 1971, 41 (Engl. Transl.)].
20. J. McKinley, A. Aponick, J. C. Raber, Ch. Fritz, D. Montgomery, and C. T. Wigal, J. Org. Chem., 1997, 62, 4874.
21. D. Liotta, M. Saindane, and C. Barnum, J. Org. Chem., 1997, 81, 3369.
22. F. Alonso and M. Yus, Tetrahedron, 1991, 47, 7471.
23. M. Takeshita, H. Tsuzuki, and M. Tashiro, Bull. Chem. Soc. Jpn., 1992, 65, 2076.
24. Structure Correlation, Eds. H.-B. Burgi and J. D. Dunitz, VCH, Weinheim - New York, 1994, 2, 768.
25. K. Krohn, H. Reiger, H. Hopf, D. Barrett, P. G. Jones, and D. Döring, Chem. Ber., 1990, 123, 1729.
26. SMART V5.051 and SAINT V5.00, Area Detector Control and Integration Software, Bruker AXS Inc., Madison (WI-53719, USA), 1998.
27. G. M. Sheldrick, SADABS, Bruker AXS Inc., Madison (WI-53719, USA), 1997.
28. G. M. Sheldrick, SHELXTL Ver.5.0. Software Reference Manual, Siemens Industrial Automation, Inc., Madison, 1995.
29. G. M. Sheldrick, SHELXTL-97, Version 5.10, Bruker AXS Inc., Madison (WI-53719, USA), 1997.