Supramolecular photochirogenesis with carbenes entrapped in cyclodextrins

European Journal of Organic Chemistry

Volumn , Issue 34, 2009, Pages 5907-5912

  Mieusset, Jean Luc ^a   Wagner, Gerald ^a   Su, Kuan Jen ^a   Steurer, Marianne ^a   Pacar, Mirjana ^a   Abraham, Michael ^a   Brinker, Udo H ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

Carbenes; Chiral induction; Cyclodextrins; Diazirines; Supramolecular chemistry

Indexed keywords

EID: 70749121703     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900899     Document Type: Article

References (46)

1. a) Photochemistry in Organized and Constrained Media (Ed.: V. Ramamurthy), Wiley, New York, 1991;
2. b) Artificial Enzymes (Ed.: R. Breslow), Wiley, New York, 2005;
3. c) For Binding Mechanisms in Supramolecular Complexes, see H.-J. Schneider, Angew. Chem. Int. Ed. 2009, 48, 3924-3977;
4. d) For Functional Molecular Flasks, see: M. Yoshizawa, J. K. Klosterman, M. Fujita, Angew. Chem. Int. Ed. 2009, 48, 3418-3438;
5. e) For chirogenesis, see G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1-73.
6. a) K. B. Yoon, Chem. Rev. 1993, 93, 321-339;
7. b) H. Garcia, H. D. Roth, Chem. Rev. 2002, 102, 3947-4008, and references cited therein.
8. a) K. Takahashi, Chem. Rev. 1998, 98, 2013-2034;
9. b) R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997-2012;
10. c) D. M. Vriezema, M. Comellas-Aragones, J. A. A. W. Elemans, J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, Chem. Rev. 2005, 105, 1445-1490.
11. a) U. H. Brinker, M. G. Rosenberg, in: Advances in Carbene Chemistry, vol.2 (Ed.: U. H. Brinker), JAI Press, Stamford, CT, 1998, pp. 29-41;
12. b) M. G. Rosenberg, U. H. Brinker, in: Adv. Phys. Org. Chem., vol.40 (Ed.: J. P. Richard), Academic Press, New York, 2005, pp. 1-47;
13. c) M. G. Rosenberg, U. H. Brinker, Eur. J. Org. Chem. 2006, 5423-5440.
14. a) R. Warmuth, J. Yoon, Acc. Chem. Res. 2001, 34, 95-105;
15. b) P. Roach, R. Warmuth, Angew. Chem. Int. Ed. 2003, 42, 3039-3042;
16. c) X. Liu, G. Chu, R. A. Moss, R. R. Sauers, R. Warmuth, Angew. Chem. Int. Ed. 2005, 44, 1994-1997.
17. M. Jones Jr., Sci. Am. 1976, 234, 101-113.
18. J.-L. Mieusset, U. H. Brinker, J. Org. Chem. 2008, 73, 1553-1558.
19. J.-L. Mieusset, A. Schrems, M. Abraham, V. B. Arion, U. H. Brinker, Tetrahedron 2009, 65, 765-770.
20. a) U. H. Brinker, G. Lin, L. Xu, W. B. Smith, J.-L. Mieusset, J. Org. Chem. 2007, 72, 8434-8451;
21. b) J.-L. Mieusset, U. H. Brinker, J. Org. Chem. 2007, 72, 10211-10219.
22. L. Trembleau Jr., J. Rebek, Science 2003, 301, 1219-1220.
23. The chiral column used produced two baseline separated peaks only for the enantiomers of 7a but not for those of 6 and 7b.
24. G. N. Fickes, C. B. Rose, J. Org. Chem. 1972, 37, 2898-2899.
25. M. T. H. Liu, Y.-K. Choe, M. Kimura, K. Kobayashi, S. Nagase, T. Wakahara, Y. Niino, M. O. Ishitsuka, Y. Maeda, T. Akasaka, J. Org. Chem. 2003, 68, 7471-7478.
26. a) W. Chidester, D. A. Modarelli, W. R. White III, D. E. Whitt, M. S. Platz, J. Phys. Org. Chem. 1994, 7, 24-27;
27. b) R. Bonneau, M. T. H. Liu, in: Advances in Carbene Chemistry, vol.2 (Ed.: U. H. Brinker), JAI Press, Stamford, CT, 1998, pp. 1-28;
28. c) X. Fu, R. A. Moss, P. Piotrowiak, M. Myahkostupov, I. R. Gould, Org. Lett. 2006, 8, 4807-4809.
29. R. Bonneau, M. T. H. Liu, J. Am. Chem. Soc. 1996, 118, 7229-7230.
30. J.-L. Mieusset, U. H. Brinker, Eur. J. Org. Chem. 2008, 3363-3368.
31. a) J.-L. Mieusset, U. H. Brinker, Chem. Listy 2004, 98, s50;
32. b) J.-L. Mieusset, D. Krois, M. Pacar, L. Brecker, G. Giester, U. H. Brinker, Org. Lett. 2004, 6, 1967-1970.
33. a) U. H. Brinker, R. Buchkremer, M. Kolodziejczyk, R. Kupfer, M. Rosenberg, M. D. Poliks, M. Orlando, M. L. Gross, Angew. Chem. 1993, 105, 1427-1429;
34. Angew. Chem. Int. Ed. Engl. 1993, 32, 1344-1346;
35. b) D. Krois, M. M. Bobek, A. Werner, H. Kählig, U. H. Brinker, Org. Lett. 2000, 2, 315-318;
36. c) D. Krois, L. Brecker, A. Werner, U. H. Brinker, Adv. Synth. Catal. 2004, 346, 1367-1374.
37. R. G. Buckeridge, K. J. Frayne, B. L. Johnson, Aust. J. Chem. 1974, 27, 1235-1244.
38. J. Kossanyi, P. Jost, B. Furth, G. Daccord, P. Chaquin, J. Chem. Res. 1980, 11, 368-369.
39. G. V. Shustov, M. T. H. Liu, K. N. Houk, Can. J. Chem. 1999, 77, 540-549.
40. C. S. Foote, R. B. Woodward, Tetrahedron 1964, 20, 687-715.
41. H. C. Brown, P. J. Geoghegan, J. Org. Chem. 1970, 35, 1844-1850.
42. M. Povárny, P. Scheiber, G. Kraiss, K. Nádor, Tetrahedron Lett. 1984, 25, 1311-1312.
43. Y. Zhang, G. B. Schuster, J. Org. Chem. 1995, 60, 7192-7197.
44. a) H. Stetter, K.-D. Rämsch, K. Elfert, Justus Liebigs Ann. Chem. 1974, 1322-1327;
45. b) T. Momose, O. Muraoka, Chem. Pharm. Bull. 1978, 26, 2217-2223;
46. c) T. Momose, O. Muraoka, S. Atarashi, T. Horita, Chem. Pharm. Bull. 1979, 27, 222-229.