A general approach to optically pure [5]-, [6]-, and [7]heterohelicenes

Angewandte Chemie - International Edition

Volumn 51, Issue 24, 2012, Pages 5857-5861

  Žádný, Jaroslav ^a   Jančařík, Andrej ^a   Andronova, Angelina ^a   Šámal, Michal ^a   Vacekchocholoušová, Jana ^a   Vacek, Jaroslav ^a   Pohl, Radek ^a   Šaman, David ^a   Císařová, Ivana ^b   Stará, Irena G ^a   Starý, Ivo ^a  

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

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

aromatic compounds; asymmetric synthesis; chirality; helical structures; heterocycles

Indexed keywords

ASYMMETRIC SYNTHESIS; CYCLOISOMERIZATIONS; DIASTEREOSELECTIVE; GENERAL APPROACH; GENERAL METHOD; HELICAL STRUCTURES; HELICENES; HETEROCYCLES; HETEROHELICENES;

AROMATIC COMPOUNDS; CATALYSIS; CHEMISTRY; CHIRALITY;

FUNCTIONAL GROUPS;

EID: 84861871496     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108307     Document Type: Article

References (44)

1. For recent reviews, see
2. Y. Shen, C.-F. Chen, Chem. Rev. 2012, 112, 1463-1535
3. I. G. Stará, I. Star, in Science of Synthesis Vol.45b (Eds.:, J.S. Siegel, Y. Tobe,), Thieme, Stuttgart, 2010, pp. 885-953
4. I. Star, I. G. Stará, in Strained Hydrocarbons (Ed.:, H. Dodziuk,), Wiley-VCH, Weinheim, 2009, pp. 166-176
5. A. Rajca, M. Miyasaka, in Functional Organic Materials (Eds.:, T.J.J. Müller, U.H.F. Bunz,), Wiley-VCH, Weinheim, 2007, pp. 547-581
6. A. Urbano, Angew. Chem. 2003, 115, 4116-4119
7. Angew. Chem. Int. Ed. 2003, 42, 3986-3989.
8. Remarkable applications of helicenes have already been reported, but the limited number of examples does not correspond to the utilization potential of these helical aromatics. For their very recent use in enantioselective catalysis, see
9. Z. Krausová, Sehnal, B. P. Bondzic, S. Chercheja, Eilbracht, I. G. Stará, D. Šaman, I. Star, Eur. J. Org. Chem. 2011, 3849-3857
10. J. Chen, B. Captain, N. Takenaka, Org. Lett. 2011, 13, 1654-1657
11. M. R. Crittall, H. S. Rzepa, D. R. Carbery, Org. Lett. 2011, 13, 1250-1253; in molecular recognition
12. K. Shinohara, Y. Sannohe, S. Kaieda, K. Tanaka, H. Osuga, H. Tahara, Y. Xu, T. Kawase, T. Bando, H. Sugiyama, J. Am. Chem. Soc. 2010, 132, 3778-3782; in self-assembly
13. M. A. Shcherbina, X. Zeng, T. Tadjiev, G. Ungar, S. H. Eichhorn, K. E. S. Phillips, T. J. Katz, Angew. Chem. 2009, 121, 7977-7980
14. Angew. Chem. Int. Ed. 2009, 48, 7837-7840; in surface science
15. P. Rahe, M. Nimmrich, A. Greuling, J. Schütte, I. G. Stará, J. Rybáček, G. Huerta-Angeles, I. Star, M. Rohlfing, A. Kühnle, J. Phys. Chem. C 2010, 114, 1547-1552; in chiral materials
16. L. Norel, M. Rudolph, N. Vanthuyne, J. A. G. Williams, C. Lescop, C. Roussel, J. Autschbach, J. Crassous, R. Réau, Angew. Chem. 2010, 122, 103-106
17. Angew. Chem. Int. Ed. 2010, 49, 99-102; in other branches of science
18. L. Adriaenssens, L. Severa, D. Koval, I. Císaová, M. MartínezBelmonte, E. C. Escudero-Adán, Novotná, Sázelová, J. Vávra, R. Pohl, D. Šaman, M. Urbanová, V. Kašička, F. Tepl, Chem. Sci. 2011, 2, 2314-2320.
19. J. Vanest, R. H. Martin, Recl. Trav. Chim. Pays-Bas 1979, 98, 113
20. T. J. Katz, A. Sudhakar, M. F. Teasley, A. M. Gilbert, W. E. Geiger, M. P. Robben, M. Wuensch, M. D. Ward, J. Am. Chem. Soc. 1993, 115, 3182-3198.
21. Y. Sawada, S. Furumi, A. Takai, M. Takeuchi, K. Noguchi, K. Tanaka, J. Am. Chem. Soc. 2012, 134, 4080-4083, and references therein
22. T. Shibata, T. Uchiyama, Y. Yoshinami, S. Takayasu, K. Tsuchikama, K. Endo, Chem. Commun. 2012, 48, 1311-1313
23. A. Latorre, A. Urbano, M. C. Carreño, Chem. Commun. 2009, 6652-6654, and references therein
24. K. Tanaka, N. Fukawa, T. Suda, K. Noguchi, Angew. Chem. 2009, 121, 5578-5581
25. Angew. Chem. Int. Ed. 2009, 48, 5470-5473
26. A. Grandbois, S. K. Collins, Chem. Eur. J. 2008, 14, 9323-9329
27. J. Caeiro, D. Peña, A. Cobas, D. Pérez, E. Guitián, Adv. Synth. Catal. 2006, 348, 2466-2474
28. M. Miyasaka, A. Rajca, M. Pink, S. Rajca, J. Am. Chem. Soc. 2005, 127, 13806-13807
29. K. Nakano, Y. Hidehira, K. Takahashi, T. Hiyama, K. Nozaki, Angew. Chem. 2005, 117, 7298-7300
30. Angew. Chem. Int. Ed. 2005, 44, 7136-7138
31. R. ElAbed, B. BenHassine, J. P. Genêt, M. Gorsane, J. Madec, L. Ricard, A. Marinetti, Synthesis 2004, 2513-2516
32. F. Tepl, I. G. Stará, I. Star, A. Kollárovič, D. Šaman, Fiedler, Š. Vyskočil, J. Org. Chem. 2003, 68, 5193-5197
33. Y. Ogawa, M. Toyama, M. Karikomi, K. Seki, K. Haga, T. Uyehara, Tetrahedron Lett. 2003, 44, 2167-2170
34. I. G. Stará, I. Star, A. Kollárovič, F. Tepl, Š. Vyskočil, D. Šaman, Tetrahedron Lett. 1999, 40, 1993-1996
35. K. Tanaka, H. Suzuki, H. Osuga, J. Org. Chem. 1997, 62, 4465-4470.
36. P. Sehnal, I. G. Stará, D. Šaman, M. Tich, J. Míšek, J. Cvačka, L. Rulíšek, J. Chocholoušová, J. Vacek, G. Goryl, M. Szymonski, I. Císaová, I. Star, Proc. Natl. Acad. Sci. USA 2009, 106, 13169-13174
37. P. Sehnal, Z. Krausová, F. Tepl, I. G. Stará, I. Star, L. Rulíšek, D. Šaman, I. Císaová, J. Org. Chem. 2008, 73, 2074-2082
38. I. G. Stará, Z. Alexandrová, F. Tepl, Sehnal, I. Star, D. Šaman, M. Buděšínsk, J. Cvačka, Org. Lett. 2005, 7, 2547-2550.
39. C. Wolf, in Dynamic Stereochemistry of Chiral Compounds, RSC Publishing, Cambridge, 2008, pp. 334-337.
40. D. A. Evans, C. J. Dinsmore, Tetrahedron Lett. 1993, 34, 6029-6032
41. R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860.
42. A. Geny, N. Agenet, L. Iannazzo, M. Malacria, C. Aubert, V. Gandon, Angew. Chem. 2009, 121, 1842-1845
43. Angew. Chem. Int. Ed. 2009, 48, 1810-1813.
44. R. H. Martin, M. J. Marchant, Tetrahedron Lett. 1972, 13, 3707-3708.