Recent developments in the synthesis of helicene-like molecules

Angewandte Chemie - International Edition

Volumn 42, Issue 34, 2003, Pages 3986-3989

  Urbano, Antonio ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Arenes; Asymmetric synthesis; Helical structures; Helicenes; Synthetic methods

Indexed keywords

DERIVATIVES; MOLECULES; SYNTHESIS (CHEMICAL);

CHIRALS;

MOLECULAR STRUCTURE;

AROMATIC COMPOUND; BENZENE DERIVATIVE; COBALT; PALLADIUM; QUINONE DERIVATIVE; RADICAL; TIN; TRANSITION ELEMENT;

BROMINATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CHIRALITY; CYCLIZATION; DIELS ALDER REACTION; ELECTRONICS; ENANTIOMER; ENANTIOSELECTIVITY; ISOMERISM; METHODOLOGY; MOLECULE; OXIDATION; PRECURSOR; REVIEW; SYNTHESIS; TECHNOLOGY;

EID: 0141676773     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200301667     Document Type: Review

References (37)

1. a) For a recent highlight on a related topic, see: C. Schmuck, Angew. Chem. 2003, 115, 2552-2556; Angew. Chem. Int. Ed. 2003, 42, 2448-2452;
2. a) For a recent highlight on a related topic, see: C. Schmuck, Angew. Chem. 2003, 115, 2552-2556; Angew. Chem. Int. Ed. 2003, 42, 2448-2452;
3. for excellent reviews on helicenes, see: b) H. Hopf, Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000, p. 321-330;
4. c) F. Vögtle, Fascinating Molecules in Organic Chemistry, Wiley, New York, 1992, p. 156-180;
5. d) K. P. Meurer, F. Vögtle, Top. Curr. Chem. 1985, 127, 1-76;
6. e) W. H. Laarhoven, W. J. Prinsen, Top. Curr. Chem. 1984, 125, 63-120;
7. f) R. H. Martin, Angew. Chem. 1974, 86, 727-738; Angew. Chem. Int. Ed. Engl. 1974, 13, 649.
8. f) R. H. Martin, Angew. Chem. 1974, 86, 727-738; Angew. Chem. Int. Ed. Engl. 1974, 13, 649.
9. a) T. J. Katz, Angew. Chem. 2000, 112, 1997-1999; Angew. Chem. Int. Ed. 2000, 39, 1921-1923;
10. a) T. J. Katz, Angew. Chem. 2000, 112, 1997-1999; Angew. Chem. Int. Ed. 2000, 39, 1921-1923;
11. b) S. Grimme, J. Harren, A. Sobanski, F. Vögtle, Eur. J. Org. Chem. 1998, 1491-1509.
12. L. Liu, B. Yang, T. J. Katz, M. K. Poindexter, J. Org. Chem. 1991, 56, 3769-3775.
13. L. Liu, T. J. Katz, Tetrahedron Lett. 1990, 31, 3983-3986.
14. For recent work, see: K. E. S. Phillips, T. J. Katz, S. Jockusch, A. J. Lovinger, N. J. Turro, J. Am. Chem. Soc. 2001, 123, 11899-11907, and references therein.
15. T. Thongpanchang, K. Paruch, T. J. Katz, A. L. Rheingold, K. Lam, L. Liable-Sands, J. Org. Chem. 2000, 65, 1850-1856.
16. M. Flammang-Barbieux, J. Nasielski, R. H. Martin, Tetrahedron Lett. 1967, 743-744.
17. M. Gingras, F. Dubois, Tetrahedron Lett. 1999, 40, 1309-1312.
18. A. Rajca, H. Wang, M. Pink, S. Rajca, Angew. Chem. 2000, 112, 4655-4657; Angew. Chem. Int. Ed. 2000, 39, 4481-4483.
19. A. Rajca, H. Wang, M. Pink, S. Rajca, Angew. Chem. 2000, 112, 4655-4657; Angew. Chem. Int. Ed. 2000, 39, 4481-4483.
20. a) D. C. Harrowven, M. I. T. Nunn, D. R. Fenwick, Tetrahedron Lett. 2002, 43, 7345-7347;
21. b) D. C. Harrowven, M. I. T. Nunn, D. R. Fenwick, Tetrahedron Lett. 2002, 43, 3189-3191.
22. a) F. Teplý, I. G. Stará, I. Starý, A. Kollárovič, D. Šaman, L. Rulíšek, P. Fiedler, J. Am. Chem. Soc. 2002, 124, 9175-9180;
23. b) I. G. Stará, I. Starý, A. Kollárović, F. Teplý, D. Šaman, P. Fiedler, Collect. Czech. Chem. Commun. 2003, 68, 917-930;
24. c) F. Teplý, I. G. Stará, I. Starý, A. Kollárovič, D. Šaman, Š. Vyskočil, P. Fiedler J. Org. Chem. 2003, 68, 5193-5197.
25. a) S. Han, A. D. Bond, R. L. Disch, D. Holmes, J. M. Schulman, S. J. Teat, K. P. C. Vollhardt, G. D. Whitener, Angew. Chem. 2002, 114, 3357-3361; Angew. Chem. Int. Ed. 2002, 41, 3223-3227;
26. a) S. Han, A. D. Bond, R. L. Disch, D. Holmes, J. M. Schulman, S. J. Teat, K. P. C. Vollhardt, G. D. Whitener, Angew. Chem. 2002, 114, 3357-3361; Angew. Chem. Int. Ed. 2002, 41, 3223-3227;
27. b) S. Han, D. R. Anderson, A. D. Bond, H. V. Chu, R. L. Disch, D. Holmes, J. M. Schulman, S. J. Teat, K. P. C. Vollhardt, G. D. Whitener, Angew. Chem. 2002, 114, 3361-3364; Angew. Chem. Int. Ed. 2002, 41, 3227-3230.
28. b) S. Han, D. R. Anderson, A. D. Bond, H. V. Chu, R. L. Disch, D. Holmes, J. M. Schulman, S. J. Teat, K. P. C. Vollhardt, G. D. Whitener, Angew. Chem. 2002, 114, 3361-3364; Angew. Chem. Int. Ed. 2002, 41, 3227-3230.
29. R. H. Janke, G. Haufe, E. U. Würthwein, J. H. Borkent, J. Am. Chem. Soc. 1996, 118, 6031-6035.
30. a) D. Peña, A. Cobas, D. Pérez, E. Guitián, L. Castedo, Org. Lett. 2003, 5, 1863-1866;
31. b) D. Peña, D. Pérez, E. Guitián, L. Castedo, Org. Lett. 1999, 1, 1555-1557.
32. a) M. C. Carreño, S. García-Cerrada, A. Urbano, J. Am. Chem. Soc. 2001, 123, 7929-7930;
33. this methodology has also been successfully applied to the enantioselective synthesis of 7,8-dihydro[4]-helicene quinones: b) M. C. Carreño, S. García-Cerrada, A. Urbano, Chem. Eur. J. 2003, 9, 4118-4131;
34. c) M. C. Carreño, M. J. Sanz-Cuesta, S. García-Cerrada, A. Urbano, Chem. Commun. 2001, 1452-1453.
35. M. C. Carreño, S. García-Cerrada, A, Urbano, Chem. Commun. 2002, 1412-1413.
36. a) Y. Ogawa, M. Toyama, M. Karikomi, K. Seki, K. Haga, T. Uyehara, Tetrahedron Lett. 2003, 44, 2167-2170;
37. b) Y. Ogawa, T. Ueno, M. Karikomi, K. Seki, K. Haga, T. Uyehara, Tetrahedron Lett. 2002, 43, 7827-7829.