Transition metal catalysed synthesis of tetrahydro derivatives of [5]-, [6]- and [7] helicene

Tetrahedron Letters

Volumn 40, Issue 10, 1999, Pages 1993-1996

  Stará, Irena G ^a   Starý, Ivo ^a   Kollárovič, Adrian ^a   Teplý, Filip ^a   Vyskočil, Štěpán ^b   Šaman, David ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

HELICENE; METAL; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; ISOMERISM; REACTION ANALYSIS; SYNTHESIS;

EID: 0033525671     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00099-4     Document Type: Article

References (23)

1. For reviews see, e. g.: (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992; p 156. (b) Meurer, K. P.; Vögtle, F. Top. Current Chem. 1985, 127, 1. (c) Laarhoven, W. H.;Prinsen, W. J. C. Top. Current Chem. 1984, 125, 63. (d) Martin, R. H. Angew. Chem. 1974, 86, 727. (e) Wynberg, H. Acc. Chem. Res. 1970, 4, 65.
2. For reviews see, e. g.: (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992; p 156. (b) Meurer, K. P.; Vögtle, F. Top. Current Chem. 1985, 127, 1. (c) Laarhoven, W. H.;Prinsen, W. J. C. Top. Current Chem. 1984, 125, 63. (d) Martin, R. H. Angew. Chem. 1974, 86, 727. (e) Wynberg, H. Acc. Chem. Res. 1970, 4, 65.
3. For reviews see, e. g.: (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992; p 156. (b) Meurer, K. P.; Vögtle, F. Top. Current Chem. 1985, 127, 1. (c) Laarhoven, W. H.; Prinsen, W. J. C. Top. Current Chem. 1984, 125, 63. (d) Martin, R. H. Angew. Chem. 1974, 86, 727. (e) Wynberg, H. Acc. Chem. Res. 1970, 4, 65.
4. For reviews see, e. g.: (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992; p 156. (b) Meurer, K. P.; Vögtle, F. Top. Current Chem. 1985, 127, 1. (c) Laarhoven, W. H.;Prinsen, W. J. C. Top. Current Chem. 1984, 125, 63. (d) Martin, R. H. Angew. Chem. 1974, 86, 727. (e) Wynberg, H. Acc. Chem. Res. 1970, 4, 65.
5. For reviews see, e. g.: (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992; p 156. (b) Meurer, K. P.; Vögtle, F. Top. Current Chem. 1985, 127, 1. (c) Laarhoven, W. H.;Prinsen, W. J. C. Top. Current Chem. 1984, 125, 63. (d) Martin, R. H. Angew. Chem. 1974, 86, 727. (e) Wynberg, H. Acc. Chem. Res. 1970, 4, 65.
6. Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211.
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10. (b) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873.
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13. For recent examples see, e. g.: (a) Stará, I. G.; Starý, I.; Tichý, M.; Závada, J.; Hanuš, V. J. Am. Chem. Soc. 1994, 116, 5084. (b) Dubois, F.; Gingras, M. Tetrahedron Lett. 1998, 39, 5039.
14. For recent examples see, e. g.: (a) Stará, I. G.; Starý, I.; Tichý, M.; Závada, J.; Hanuš, V. J. Am. Chem. Soc. 1994, 116, 5084. (b) Dubois, F.; Gingras, M. Tetrahedron Lett. 1998, 39, 5039.
15. Stará, I. G.; Starý, I.; Kollárovič, A.; Teplý, F.; Šaman, D.; Tichý, M. Chimia 1997, 51, 378.
16. (b) Stará, I. G.; Starý, I.; Kollárovič, A.; Teplý, F.; Šaman, D.; Tichý, M. J. Org. Chem. 1998, 63, 4046.
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19. 3/TMS): 2.62-3.00 (m, 8 H), 6.91 (dt, 2 H, J = 7.7, 7.7, 1.5 Hz), 7.10 (s, 2 H), 7.10 (dt, 2 H, J = 7.5, 7.5, 1.3 Hz), 7.22 (dd, 2 H, J = 7.9, 1.5 Hz), 7.25 (dd, 2 H, J = 7.5, 1.3 Hz).
20. 3/TMS): 2.66 (ddt, 1 H, J = 15.0, 4.3, 1.4, 1.4 Hz), 2.69 (ddt, 1 H, J = 15.2, 4.4, 1.4, 1.4 Hz), 2.75 (ddt, 1 H, J = 15.2, 4.4, 1.4, 1.4 Hz), 2.86 (ddd, 1 H, J = 14.8, 4.3, 2.2 Hz), 2.88 (ddt, 1 H, J = 14.1, 4.1, 2.0, 2.0 Hz), 2.91 (ddd, 1 H, J = 15.2, 4.5, 2.1 Hz), 3.01 (brddd, 1 H, J = 14.7, 10.1, 4.2 Hz), 3.04 (brddd, 1 H, J = 14.2, 10.0, 4.4 Hz), 6.34 (ddt, 1 H, J = 7.8, 6.8, 1.2, 1.2 Hz), 6.36 (dd, 1 H, J = 7.8, 1.9 Hz), 6.81 (ddd, 1 H, J = 7.4, 6.8, 1.9 Hz), 6.84 (ddd, 1 H, J = 8.3, 6.8, 1.3 Hz), 7.10 (ddd, J = 8.0, 6.8, 1.2 Hz), 7.15 (dq, 1 H, J = 7.3, 0.8, 0.8, 0.8 Hz), 7.20 (dd, 1 H, J = 7.4, 1.0 Hz), 7.25 (dd, 1 H, J = 7.4, 1.0 Hz), 7.47 (d, 1 H, J = 8.0 Hz), 7.47 (dq, 1 H, J = 8.5, 1.0, 1.0, 1.0 Hz), 7.64 (brd, 1 H, J = 8.1 Hz), 7.70 (brd, 1 H, J = 8.2 Hz).
21. 3/TMS): 2.76 (dddd, 2 H, J = 15.8, 14.9, 4.1, 1.3 Hz), 2.96 (ddd, 2 H, J = 14.8, 4.1, 2.0 Hz), 2.99 (ddd, 2 H, J = 15.8, 4.2, 2.0 Hz), 3.10 (ddd, 2 H, J = 14.9, 14.8, 4.2 Hz), 6.53 (ddd, 2 H, J = 8.6, 6.8, 1.3 Hz), 6.82 (ddd, 2 H, J = 8.1, 6.8, 1.2 Hz), 6.96 (dddd, 2 H, J = 8.6, 1.3, 1.2, 0.7 Hz), 7.20 (ddd, 2 H, J = 8.1, 1.3, 0.7 Hz), 7.33 (dd, 2 H, J = 8.2, 1.0 Hz), 7.34 (s, 2 H), 7.34 (d, 2 H, J = 8.2 Hz).
22. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945.
23. Enantiomers of 13 were separated by HPLC on a chiral column ((R,R)-Whelk-O1, Merck).