Metal complexes of a biconcave porphyrin with D4-structure - Versatile chiral shift agents

Chemistry - A European Journal

Volumn 7, Issue 12, 2001, Pages 2676-2686

  Schwenninger, Reinhold ^a   Schlögl, Johann ^a   Maynollo, Josef ^a   Gruber, Karl ^b   Ochsenbein, Philippe ^c   Bürgi, Hans Beat ^c   Konrat, Robert ^a   Kräutler, Bernhard ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b UNIVERSITY OF GRAZ   (Austria)

^c UNIVERSITY OF BERN   (Switzerland)

Author keywords

Cage compounds; Chiral shift reagent; Fullerenes; Porphyrinoids; Structure elucidation

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; CARBON; COBALT; ESTER; FULLERENE DERIVATIVE; METAL COMPLEX; METALLOPORPHYRIN; NITRILE; PORPHYRIN; RHENIUM COMPLEX; RUTHENIUM COMPLEX; ZINC COMPLEX;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0035907736     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010618)7:12<2676::AID-CHEM26760>3.0.CO;2-I     Document Type: Article

References (64)

1. R. Schwenninger, Y. Ramondenc, K. Wurst, J. Schlögl, B. Kräutler, Chem. Eur. J. 2000, 6, 1214-1223.
2. a) Y. Ramondenc, R. Schwenninger, T. Phan, K. Gruber, C. Kratky, B. Kräutler, Angew. Chem. 1994, 106, 939-941;
3. Angew. Chem. Int. Ed. Engl. 1994, 33, 889-891;
4. b) J. Schlögl, B. Kräutler, Synlett 1999, S1, 969-971.
5. a) H. Ogoshi, T. Mizutani, Acc. Chem. Res. 1998, 31, 81-89;
6. b) K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344.
7. a) J. T. Groves, P. Viski, J. Org. Chem. 1990, 55, 3628-3634;
8. b) M. Komatsu, T. Aida, S. Inoue, J. Am. Chem. Soc. 1991, 113, 8492-8498;
9. c) J. P. Collman, V. J. Lee, C. J. Kellen-Yuen, X. Zhang, J. A. Ibers, J. I. Brauman, J. Am. Chem. Soc. 1995, 117, 692-703;
10. d) L. A. Campbell, T. Kodadek, J. Mol. Catal. A 1996, 113, 293-310;
11. e) B. R. Cook, T. J. Reinert, K. S. Suslick, J. Am. Chem. Soc. 1986, 108, 7281-7286.
12. a) Y. Naruta, Metalloporphyrins in Catalytic Oxidations (Ed.: R. A. Sheldon), Dekker, New York, 1994, pp. 241-259;
13. b) E. N. Jacobsen, Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, pp. 159-202;
14. c) J. P. Collman, Z. Wang, Chemtracts: Org. Chem. 1999, 12, 229-263.
15. a) R. L. Halterman, S.-T. Jan, J. Org. Chem. 1991, 56, 5253-5254;
16. b) J. Barry, T. Kodadek, Tetrahedron Lett. 1994, 35, 2465-2468.
17. a) J. P. Collman, P. S. Wagenknecht, J. E. Hutchinson, Angew. Chem. 1994, 106, 1620-1639;
18. Angew. Chem. 1994, 33, 1537-1554;
19. b) R. Guilard, K. M. Kadish, Chem. Rev. 1988, 88, 1121-1146.
20. a) J. T. Groves, J. S. Roman, J. Am. Chem. Soc. 1995, 117, 5594-5595;
21. b) W.-H. Leung, C.-M. Che, J. Am. Chem. Soc. 1989, 111, 8812-8818.
22. a) S. O'Malley, T. Kodadek, Organometallics 1992, 11, 2299-2302;
23. b) B. B. Wayland, A. E. Sherry, G. Poszmik, A. G. Bunn, J. Am. Chem. Soc. 1992, 114, 1613-1681.
24. See for example, a) P. Schreier, A. Bernreuther, M. Huffer, Analysis of Chiral Organic Compounds, de Gruyter, Berlin, 1995, p. 42;
25. b) D. Parker, Chem. Rev. 1991, 91, 1441-1457;
26. c) G. R. Sullivan, Top. Stereochem. 1978, 10, 287-329.
27. J. W. Buchler, The Porphyrins, Vol. I (Ed.: D. Dolphin), Academic Press, New York, 1978, pp. 390-485.
28. T. Ema , M. O. Senge, N. Y. Nelson, H. Ogoshi, K. M. Smith, Angew. Chem. 1994, 106, 1951-1953;
29. Angew. Chem. Int. Ed. Engl. 1994, 33, 1879-1881.
30. T. Boschi, S. Licoccia, R. Paolesse, P. Tagliatesta, Inorg. Chim Acta 1989, 163, 135-137.
31. M. Barley, J. Y. Becker, G. Domazetis, D. Dolphin, B. R. James, Can. J. Chem. 1983, 61, 2389-2396.
32. G. N. La Mar, F. A. Walker, The Porphyrins, Vol. IV (Ed.: D. Dolphin), Academic Press, New York, 1979, pp. 61-155.
33. a) D. J. Craik, J. A. Wilce, Methods in Molecular Biology, Vol. 60 (Ed.: D. G. Reid), Humana, Totowa, 1997, p. 195;
34. b) J. Schlögl, Dissertation, University of Innsbruck, September 1999.
35. a) B. Kräutler, T. Müller, A. Duarte, Chem. Eur. J. 2001, 7, in press;
36. b) B. Kräutler, Fullerenes: Recent Advances, Vol. III (Eds.: K. M. Kadish, R. S. Ruoff), Electrochemical Society, Pennington, 1996, pp. 1284-1295;
37. c) A. Duarte-Ruiz, T. Müller, K. Wurst, B. Kräutler, Tetrahedron, in press.
38. J. A. Shelnutt, X.-Z. Song, J.-G. Ma, S.-L. Jia, W. Jentzen, C. J. Medforth, Chem. Soc. Rev. 1998, 27, 31-41.
39. a) C. Kratky, R. Waditschatka, C. Angst, J. E. Johansen, J. C. Plaquevent, J. Schreiber, A. Eschenmoser, Helv. Chim. Acta 1985, 68, 1312-1337;
40. b) E. F. Meyer, D. L. Cullen, The Porphyrins, Vol III (Ed.: D. Dolphin), Academic Press, New York, 1978, pp. 513-529;
41. c) W. R. Scheldt, The Porphyrins, Vol III (Ed.: D. Dolphin), Academic Press, New York, 1978, pp. 463-511;
42. d) D. J. Nurco, C. J. Medforth, T. P. Forsyth, M. M. Olmstead, K. M. Smith, J. Am. Chem. Soc. 1996, 118, 10918-10919.
43. a) R. J. Abraham, G. R. Bedford, B. Wright, Org. Magn. Reson. 1982, 18, 45;
44. b) D. Toronto, F. Sarrazin, J. Pecaut, J.-C. Marchon, M. Shang, W. R. Scheldt, Inorg. Chem. 1998, 37, 526-532.
45. T. S. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383.
46. a) P. D. W. Boyd, M. C. Hodgson, C. E. F. Rickard, A. G. Oliver, L. Chaker, P. J. Brothers, R. D. Nolskar, F. S. Tham, C. A. Reed, J. Am. Chem. Soc. 1999, 121, 10487-10495;
47. b) M. M. Olmstead, D. A. Costa, K. Maitra, B. C. Noll, S. L. Phillips, P. M. Van Calcar, A. L. Balch, J. Am. Chem. Soc. 1999, 121, 7090-709.
48. J. Xiao, M. R. Savina, G. B. Martin, A. H. Francis, M. E. Meyerhoff, J. Am. Chem. Soc. 1994, 116, 9341-9342.
49. Reviewed in, for example: a) F. Diederich, M. Gomez-Lopez, Chem. Soc. Rev. 1999, 28, 263-277;
50. b) A. L. Balch, M. M. Olmstead, Chem. Rev. 1998, 95, 2123-2165.
51. F. Diederich, Angew. Chem. 1988, 100, 372-396;
52. Angew. Chem. Int. Ed. Engl. 1988, 27, 362-386.
53. a) L. T. Scott, H. E. Bronstein, D. V. Preda, R. B. M. Ansems, M. S. Bratcher, S. Hagen, Pure Appl. Chem. 1999, 71, 209-219;
54. b) F. G. Klärner, U. Burkert, M. Kamieth, R. Boese, J. Benet-Buchholz, Chemistry 1999, 5, 1700-1707.
55. a) B. Kräutler, T. Müller, J. Maynollo, K. Gruber, P. Ochsenbein, D. Schwarzenbach, H.-B. Bürgi, Angew. Chem. 1996, 108, 1294-1296;
56. Angew. Chem. Int. Ed. Engl. 1996, 35, 1204-1206;
57. b) J. L. Atwood, G. A. Koutsantonis, C. L. Raston, Nature 1994, 368, 229-231;
58. c) P. C. Andrews, J. L. Atwood, L. J. Barbour, P. J. Nichols, C. L. Raston Chemistry 1998, 4, 1384-1387;
59. d) T. Haino, M. Yanase, Y. Fukazawa, Angew. Chem. 1998, 110, 1044-1046;
60. Angew. Chem. Int. Ed. 1998, 37, 997-998.
61. A. Bax, S. Subramanian, J. Magn. Reson. 1986, 67, 565.
62. G. M. Sheldrick, SHELXL97 1997, University of Göttingen, Germany.
63. H.-B. Bürgi, E. Blanc, D. Schwarzenbach, S. Liu, Y. Lu, M. M. Kappes, J. A. Ibers, Angew. Chem. 1992, 104, 667-669;
64. Angew. Chem. Int. Ed. 1992, 31, 640-643.