Deracemization of a macrocyclic 1,1′-biisoquinoline

Helvetica Chimica Acta

Volumn 91, Issue 5, 2008, Pages 904-913

  Dyker, Gerald ^a   Stirner, Wolfgang ^a   Henkel, Gerald ^b   Schreiner, Peter R ^c  

^a RUHR UNIVERSITY BOCHUM   (Germany)

^b UNIVERSITY OF PADERBORN   (Germany)

^c JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS;

CAMPHORSULFONIC ACIDS; DERACEMIZATION; MACROCYCLIC;

OPTICAL DEVICES;

ALDEHYDE; BIISOQUINOLINE; MACROCYCLIC COMPOUND; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTAL STRUCTURE; PRIORITY JOURNAL; QUANTUM YIELD; RACEMIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 55549125233     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200890095     Document Type: Article

References (63)

1. R. Noyori, Adv. Synth. Catal. 2003, 345, 15;
2. M. Berthod, G. Mignani, G. Woodward, M. Lemaire, Chem. Rev. 2005, 105, 1801;
3. J. G. Strong, PharmaChem 2003, 2, 20;
4. H. Kumobayashi, T. Miura, N. Sayo, T. Saito, X. Zhang, Synlett 2001, 1055.
5. M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269;
6. J. M. Brunel, Chem. Rev. 2005, 105, 857;
7. P. W. H. Chan, Y. Yamamoto, Chemtracts 2000, 13, 14.
8. I. J. S. Fairlamb, Annu. Rep., Sect. B 2003, 99, 104;
9. A. C. Humphries, A. Pfaltz, 'Enantioselective Catalysis Using Sterically and Electronically Unsymmetrical Ligands', in 'Stimulating Concepts in Chemistry', Eds. F. Vögtle, J. F. Stoddart, M. Shibasaki, Wiley-VCH, Weinheim, 2000, p. 89-103;
10. H. Brunner, 'Chemical Synthesis: Gnosis to Prognosis', in 'NATO ASI Series, Series E: Applied Sciences', Eds. C. Chatgilialoglu, V. Snieckus, Kluwer Academic Publishers, 1996, Vol. 320, pp. 175-190;
11. J.-P. Genet, in 'Advanced Asymmetric Synthesis', Ed. G. R. Stephenson, Blackie, Glasgow, 1996, pp. 146-180.
12. N. W. Alcock, J. M. Brown, D. I. Hulmes, Tetrahedron: Asymmetry 1993, 4, 743;
13. N. Gommermann, P. Knochel, Chem. Commun. 2005, 4175;
14. C. W. Lim, O. Tissot, A. Mattison, M. W. Hooper, J. M. Brown, A. R. Cowley, D. I. Hulmes, A. J. Blacker, Org. Process Res. Dev. 2003, 7, 379;
15. H. Doucet, E. Fernandez, T. P. Layzell, J. M. Brown, Chem.-Eur. J. 1999, 5, 1320.
16. A. Korostylev, I. Gridnev, J. M. Brown, J. Organomet. Chem. 2003, 680, 329.
17. S. Oi, K.Kawagoe, S. Miyano, Chem. Lett. 1993, 22, 79;
18. G. Bringmann, M. Heubes, M. Breuning, L. Göbel, M. Ochse, B.Schöner, O. Schupp, J. Org. Chem. 2000, 65, 722.
19. G. Bringmann, M. Breuning, S. Tasler, Synthesis 1999, 525.
20. G. Dyker, B. Hölzer, G. Henkel, Tetrahedron: Asymmetry 1999, 10, 3297.
21. K. Yamamoto, H. Tateishi, K. Watanabe, T. Adachi, H. Matsubara, T. Ueda, T. Yoshida, Chem. Commun. 1995, 1637;
22. K. Yamamoto, K. Watanabe, H. Chikamatsu, Y. Okamoto, T. Yoshida, Chem. Commun. 1987, 807.
23. G. Dyker, J. Körning, W. Stirner, Eur. J. Org. Chem. 1998, 149.
24. C. Pomeranz, Monatsh. Chem. 1893, 14, 116;
25. P. Fritsch, Justus Liebigs Ann. Chem. 1895, 286, 1;
26. W. J. Gensler, Org. React. 1951, 6, 191.
27. K. Kido, Y. Watanabe, Heterocycles 1980, 14, 1151.
28. P. M. Dharmasena, P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1 1994, 35, 7119.
29. J. B. Hendrickson, C. Rodriguez, J. Org. Chem. 1983, 48, 3344.
30. K. Matsumoto, K. Otsuka, T. Okamoto, H. Mogi, Synlett 2007, 729;
31. S. Borocci, F. Ceccacci, L. Galantini, G. Mancini, D. Monti, A. Scipioni, M. Venanzi, Chirality 2003, 15, 441;
32. E. Tobler, M. Lammerhofer, G. Mancini, W. Lindner, Chirality 2001, 13, 641.
33. R. Noyori, M. Tokunaga, M. Kitamura, Bull. Chem. Soc. Jpn. 1995, 68, 36;
34. S. R. Ward, Tetrahedron: Asymmetry 1995, 6, 1475;
35. S. Caddick, K. Jenkins, Chem. Soc. Rev. 1996, 25, 447;
36. J. Liang, J. Ruble, G. C. Fu, J. Org. Chem. 1998, 63, 3154;
37. H. Pellissier, Tetrahedron 2003, 59, 8291;
38. B. Martin-Matute, J.-E. Baeckvall, Curr. Opin. Chem. Biol. 2007, 11, 226.
39. W. Stirner, Ph.D. Thesis, Duisburg University, 1999.
40. N. Harada, K. Nakanishi, 'Circular Dichroic Spectroscopy Exciton Coupling in Organic Stereochemistry', University Science Books, Mill Valley, 1983, p. 201.
41. K. Nakanishi, M. Ohashi, S. Kumasaki, H. Koike, Bull. Chem. Soc. Jpn. 1961, 34, 533;
42. H. Tsue, H. Fujinami, T. Tsuchiya, R. Itakura, K. Takahashi, H. Kobayashi, K. Hirao, Chem. Lett. 1999, 17.
43. D. Parker, Chem. Rev. 1991, 91, 1441.
44. B. A. Sweetman, H. Müller-Bunz, P. J. Guiry, Tetrahedron Lett. 2005, 46, 4643.
45. C. W. N. Cumper, S. K. Dev, S. R. Landor, J. Chem. Soc., Perkin Trans. 2 1973, 537.
46. A. Malkov, P. Kocovsky, Eur. J. Org. Chem. 2007, 29;
47. P. Kocovsky, A. Malkov, Enantiosel. Organocatal. 2007, 255;
48. B. Qin, X. Liu, J. Shi, K. Zheng, H. Zhao, X. Feng, J. Org. Chem. 2007, 72, 2374;
49. J. Huang, X. Liu, Y. Wen, B. Qin, X. Feng, J. Org. Chem. 2007, 72, 204;
50. G. Chelucci, N. Belmonte, M. Benaglia, L. Pignataro, Tetrahedron Lett. 2007, 48, 4037;
51. S. E. Denmark, Y. Fan, M. D. Eastgate, J. Org. Chem. 2005, 70, 5235;
52. M. Nakajima, T. Yokota, M. Saito, S. Hashimoto, Tetrahedron Lett. 2004, 45, 61;
53. A. V. Malkov, L. Dufkova, L. Farrugia, P. Kocovsky, Angew. Chem., Int. Ed. 2003, 42, 3674;
54. B. Liu, X. Feng, F. Chen, G. Zhang, X. Cui, Y. Jiang, Synlett 2001, 1551;
55. M. Saito, M. Nakajima, S. Hashimoto, Chem. Commun. 2000, 1851;
56. G. Chelucci, A. Bacchi, D. Fabbri, A. Saba, F. Ulgheri, Tetrahedron Lett. 1999, 40, 553.
57. A. D. Becke, Phys. Rev. A 1988, 38, 3098.
58. J. P. Perdew, Y. Wang, Phys. Rev. B 1992, 23, 5048.
59. T. H. Dunning Jr., J. Chem. Phys. 1989, 90, 1007.
60. P. R. Schreiner, A. A. Fokin, R. A. Pascal, A. de Meijere, Org. Lett. 2006, 8, 3635;
61. P. R. Schreiner, Angew. Chem., Int. Ed. 2007, 23, 4217;
62. M. D. Wodrich, C. Corminboeuf, P. R. Schreiner, A. A. Fokin, P. von Ragué Schleyer, Org. Lett. 2007, 9, 1851.
63. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision D2, Pittsburgh, 2003.