Crystallization-induced dynamic resolution of stereolabile biaryl derivatives involving supramolecular interactions

Crystal Growth and Design

Volumn 12, Issue 6, 2012, Pages 2719-2723

  Degenbeck, H ^a   Felten, A S ^a   Etxebarria, J ^a   Escudero Adan E C ^a   Benet Buchholz, J ^a   Vidal Ferran, A ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,2-DIAMINE; COPPER COMPLEXES; CRYSTALLIZATION-INDUCED DYNAMIC RESOLUTIONS; CU COMPLEXES; DIAMINE LIGANDS; DIAMINE MOIETIES; ENANTIOPURE; HYDROGEN BONDING INTERACTIONS; MOLECULAR LEVELS; STEREO-SELECTIVE; STEREOGENIC AXIS; STEREOLABILE; SUPRAMOLECULAR INTERACTIONS; SYNTHETIC STRATEGIES;

CHIRALITY; ENANTIOMERS; HYDROGEN BONDS; LIGANDS; METHANOL; SUPRAMOLECULAR CHEMISTRY; X RAY DIFFRACTION;

COPPER COMPOUNDS;

EID: 84861909092     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg300044v     Document Type: Article

References (42)

1. In Comprehensive Asymmetric Catalysis, 1 st ed.; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vols. I - III.
2. In Comprehensive Asymmetric Catalysis: Supplements I and II, 1 st ed.; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 2004.
3. Borovkov, V. V.; Hembury, G. A.; Inoue, Y. Acc. Chem. Res. 2004, 37, 449
4. Ernst, K.-H. Top. Curr. Chem. 2006, 265, 209
5. Hembury, G. A.; Borovkov, V. V.; Inoue, Y. Chem. Rev. 2008, 108, 1
6. Szumna, A. Chem. Soc. Rev. 2010, 39, 4274
7. Lee, S. J.; Lin, W. Acc. Chem. Res. 2008, 41, 521
8. Ballester, P.; Vidal-Ferran, A. In Supramolecular Catalysis; van Leeuwen, P. W. N. M., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2008; p 1.
9. Meeuwissen, J.; Reek, J. N. H. Nat. Chem. 2010, 2, 615
10. Ballester, P.; Vidal-Ferran, A.; van Leeuwen, P. W. N. M. In Modern Strategies in Supramolecular Catalysis; Gates, B. C.; Knözinger, H.; Jentoft, F., Eds.; Advances in Catalysis; Academic Press: U.K., 2011; Vol. 54, pp 63-126.
11. Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 6929
12. Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297
13. Borovkov, V. V.; Hembury, G. A.; Inoue, Y. Angew. Chem., Int. Ed. 2003, 42, 5310
14. Kubo, Y.; Ishii, Y.; Yoshizawa, T.; Tokita, S. Chem. Commun. 2004, 1394
15. de Jong, J. J. D.; Lucas, L. N.; Kellogg, R. M.; van Esch, J. H.; Feringa, B. L. Science 2004, 304, 278
16. Eelkema, R.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127, 13480
17. Hou, J.-L.; Yi, H.-P.; Shao, X.-B.; Li, C.; Wu, Z.-Q.; Jiang, X.-K.; Wu, L.-Z.; Tung, C.-H.; Li, Z.-T. Angew. Chem., Int. Ed. 2006, 45, 796
18. Takagi, H.; Mizutani, T.; Horiguchi, T.; Kitagawa, S.; Ogoshi, H. Org. Biomol. Chem. 2005, 3, 2091
19. Ikeda, C.; Yoon, Z. S.; Park, M.; Inoue, H.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2005, 127, 534
20. Ishii, Y.; Soeda, Y.; Kubo, Y. Chem. Commun. 2007, 2953
21. Etxebarria, J.; Vidal-Ferran, A.; Ballester, P. Chem. Commun. 2008, 5939
22. Haino, T.; Tanaka, M.; Fukazawa, Y. Chem. Commun. 2008, 468
23. Etxebarria, J.; Degenbeck, H.; Felten, A. S.; Serres, S.; Nieto, N.; Vidal-Ferran, A. J. Org. Chem. 2009, 74, 8794
24. Wezenberg, S. J.; Salassa, G.; Escudero-Adan, E. C.; Benet-Buchholz, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2011, 50, 713
25. Huang, Z.; Kang, S.-K.; Lee, M. J. Mater. Chem. 2011, 21, 15327
26. See for example: Wolf, C. Dynamic Stereochemistry of Chiral Compounds: Principles and Applications; The Royal Society of Chemistry: Cambridge, U.K., 2008.
27. Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447
28. Ebbers, E. J.; Ariaans, G. J. A.; Houbiers, J. P. M; Bruggink, A.; Zwanenburg, B. Tetrahedron 1997, 53, 9417
29. Anderson, N. G. Org. Process Res. Dev. 2006, 10, 683
30. Kosmrlj, J.; Weigel, L. O.; Evans, D. A.; Downey, C. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 3208
31. Chen, J. G.; Zhu, J.; Skonezny, P. M.; Rosso, V.; Venit, J. J. Org. Lett. 2004, 6, 3233
32. Kiau, S.; Discordia, R. P.; Madding, G.; Okuniewicz, F. J.; Rosso, V.; Venit, J. J. J. Org. Chem. 2004, 69, 4256
33. Marchalin, S.; Cvopova, K.; Kriz, M.; Baran, P.; Oulyadi, H.; Daich, A. J. Org. Chem. 2004, 69, 4227
34. Xu, H.-W.; Wang, Q.-W.; Zhu, J.; Deng, J.-G.; Cun, L.-F.; Cui, X.; Wu, J.; Xu, X.-L.; Wu, Y.-L. Org. Biomol. Chem. 2005, 3, 4227
35. Ikunaka, M.; Kato, S.; Sugimori, D.; Yamada, Y. Org. Process Res. Dev. 2007, 11, 73
36. Yanagisawa, A.; Nishimura, K.; Ando, K.; Nezu, T.; Maki, A.; Kato, S.; Tamaki, W.; Imai, E.; Mohri, S.-I. Org. Process Res. Dev. 2010, 14, 1182
37. Herradon, B.; Montero, A.; Mann, E.; Maestro, M. A. CrystEngComm 2004, 6, 512
38. Altamura, M.; Guidi, A.; Jierry, L.; Paoli, P.; Rossi, P. CrystEngComm 2011, 13, 2310
39. Patel, M. J.; Trivedi, B. M. J. Chem. Res. 2004, 198
40. 2- 3, respectively
41. Andra, K.; Fleischer, F. Z. Anorg. Allg. Chem. 1982, 485, 210
42. -1: Sahnoun, R.; Koseki, S.; Fujimura, Y. J. Phys. Chem. A 2006, 110, 2440