Planar chiral tetrasubstituted [2.2]paracyclophane: Optical resolution and functionalization

Journal of the American Chemical Society

Volumn 136, Issue 9, 2014, Pages 3350-3353

  Morisaki, Yasuhiro ^a   Gon, Masayuki ^a   Sasamori, Takahiro ^a   Tokitoh, Norihiro ^a   Chujo, Yoshiki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

CHIRAL BUILDING BLOCKS; CHIROPTICAL PROPERTIES; CIRCULARLY POLARIZED LUMINESCENCE; FLUORESCENCE QUANTUM EFFICIENCY; FUNCTIONALIZATIONS; MACROCYCLIC COMPOUNDS; OPTICAL RESOLUTION; [2.2]PARACYCLOPHANE;

CHEMISTRY;

CYCLOPHANE; MACROCYCLIC COMPOUND; PARACYCLOPHANE DERIVATIVE;

ABSORPTION; ANALYSIS; ARTICLE; CATALYSIS; CHIRALITY; COLUMN CHROMATOGRAPHY; CONFORMATIONAL TRANSITION; CRYSTALLIZATION; DESILYLATION; DIASTEREOISOMER; ENANTIOMER; ENVIRONMENT; HYDROLYSIS; LUMINESCENCE; MASS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL RESOLUTION; OXIDATIVE COUPLING; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84897732303     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja412197j     Document Type: Article

References (43)

1. Cyclophane Chemistry: Synthesis, Structures and Reactions; Vögtle, F., Ed.; John Wiley & Sons: Chichester, 1993.
2. Modern Cyclophane Chemistry; Gleiter, R., Hopf, H., Eds.; Wiley-VCH: Weinheim, 2004.
3. Cram, D. J.; Allinger, N. L. J. Am. Chem. Soc. 1955, 77, 6289-6294
4. Rozenberg, V.; Sergeeva, E.; Hopf, H. In Modern Cyclophane Chemistry, Gleiter, R.; Hopf, H., Eds.; Wiley-VCH: Weinheim, 2004; pp 435-462.
5. Rowlands, G. J. Org. Biomol. Chem. 2008, 6, 1527-1534
6. Gibson, S. E.; Knight, J. D. Org. Biomol. Chem. 2003, 1, 1256-1269
7. Aly, A. A.; Brown, A. B. Tetrahedron 2009, 65, 8055-8089
8. Paradies, J. Synthesis 2011, 3749-3766
9. Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207-6208
10. Rossen, K.; Pye, P. J.; Maliakal, A.; Volante, R. P. J. Org. Chem. 1997, 62, 6462-6463
11. Zhuravsky, R.; Starikova, Z.; Vorontsov, E.; Rozenberg, V. Tetrahedron: Asymmetry 2008, 19, 216-222
12. Jiang, B.; Zhao, X.-L. Tetrahedron: Asymmetry 2004, 15, 1141-1143
13. Jones, P. G.; Hillmer, J.; Hopf, H. Acta Crystallogr. 2003, E59, o24-o25
14. Pamperin, D.; Hopf, H.; Syldatk, C.; Pietzsch, M. Tetrahedron: Asymmetry 1997, 8, 319-325
15. Pamperin, D.; Ohse, B.; Hopf, H.; Pietzsch, M. J. Mol. Catal. B: Enzymatic 1998, 5, 317-319
16. Braddock, D. C.; MacGilp, I. D.; Perry, B. G. J. Org. Chem. 2002, 67, 8679-8681
17. Morisaki, Y.; Hifumi, R.; Lin, L.; Inoshita, K.; Chujo, Y. Chem. Lett. 2012, 41, 990-992
18. Meyer-Eppler, G.; Vogelsang, E.; Benkhäuser, C.; Schneider, A.; Schnakenburg, G.; Lützen, A. Eur. J. Org. Chem. 2013, 4523-4532
19. Morisaki, Y.; Hifumi, R.; Lin, L.; Inoshita, K.; Chujo, Y. Polym. Chem. 2012, 3, 2727-2730
20. Optical resolution of rac-4,5,15,16-tetrasubstituted [2.2]paracyclophane was reported: Vorontsova, N. V.; Rozenberg, V. I.; Sergeeva, E. V.; Vorontsov, E. V.; Starikova, Z. A.; Lyssenko, K. A.; Hopf, H. Chem.-Eur. J. 2008, 14, 4600-4617
21. Hopf, H. Angew. Chem., Int. Ed. 2008, 47, 9808-9812
22. Carbon-Rich Compounds; Haley, M. M.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, 2006.
23. Review on chiral carbon-rich macrocycles: Campbell, K.; Tykwinski, R. R. In Carbon-Rich Compounds: From Molecules to Materials; Haley, M. M.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, 2006; pp 229-294.
24. Chow, H.-F.; Low, K.-H.; Wong, K. Y. Synlett 2005, 2130-2134
25. Tohda, Y.; Sonogashira, K.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470
26. Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; pp 493-529.
27. Bondarenko, L.; Dix, I.; Hinrichs, H.; Hopf, H. Synthesis 2004, 2751-2759
28. Schultz, A.; Li, X.; Barkakaty, B.; Moorefield, C. N.; Wesdemiotis, C.; Newkome, G. R. J. Am. Chem. Soc. 2012, 134, 7672-7675
29. Hinrichs, H.; Boydston, A. J.; Jones, P. G.; Hess, K.; Herges, R.; Haley, M. M.; Hopf, H. Chem.-Eur. J. 2006, 12, 7103-7115
30. Wang, S.; Bazan, G. C.; Tretiak, S.; Mukamel, S. J. Am. Chem. Soc. 2000, 122, 1289-1297
31. Bartholomew, G. P.; Bazan, G. C. Acc. Chem. Res. 2001, 34, 30-39
32. Bartholomew, G. P.; Bazan, G. C. Synthesis 2002, 1245-1255
33. Hong, J. W.; Woo, H. Y.; Bazan, G. C. J. Am. Chem. Soc. 2005, 127, 7435-7443
34. Bazan, G. C. J. Org. Chem. 2007, 72, 8615-8635
35. -3): Field, J. E.; Muller, G.; Riehl, J. P.; Venkataraman, D. J. Am. Chem. Soc. 2003, 125, 11808-11809
36. -3): Kawai, T.; Kawamura, K.; Tsumatori, H.; Ishikawa, M.; Naito, M.; Fujiki, M.; Nakashima, T. ChemPhysChem 2007, 8, 1465-1468
37. Tsumatori, H.; Nakashima, T.; Kawai, T. Org. Lett. 2010, 12, 2362-2365
38. -2): Kaseyama, T.; Furumi, S.; Zhang, X.; Tanaka, K.; Takeuchi, M. Angew. Chem., Int. Ed. 2011, 50, 3684-3687
39. -3): Maeda, H.; Bando, Y.; Shimomura, K.; Yamada, I.; Naito, M.; Nobusawa, K.; Tsumatori, H.; Kawai, T. J. Am. Chem. Soc. 2011, 133, 9266-9269
40. -2): Haketa, Y.; Bando, Y.; Takaishi, K.; Uchiyama, M.; Muranaka, A.; Naito, M.; Shibaguchi, H.; Kawai, T.; Maeda, H. Angew. Chem., Int. Ed. 2012, 51, 7967-7971
41. -2): Sawada, Y.; Furumi, S.; Takai, A.; Takeuchi, M.; Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2012, 134, 4080-4083
42. -3): Oyama, H.; Nakano, K.; Harada, T.; Kuroda, R.; Naito, M.; Nobusawa, K.; Nozaki, K. Org. Lett. 2013, 15, 2104-2107
43. Review, see: Maeda, H.; Bando, Y. Pure Appl. Chem. 2013, 85, 1967-1978 Technology