A highly enantiopure biconcave porphyrin with effective D4-structure

Chemistry - A European Journal

Volumn 6, Issue 7, 2000, Pages 1214-1223

  Schwenninger, Reinhold ^a,b   Ramondenc, Yvan ^a,c   Wurst, Klaus ^a   Schlögl, Johann ^a   Kräutler, Bernhard ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b Fluka Chemie AG   (Switzerland)

^c UNIVERSITÉ DE ROUEN   (France)

Author keywords

Asymmetric synthesis; Cage compounds; Chirality; Porphyrinoids; Structure elucidation

Indexed keywords

PORPHYRIN; PYRROLE DERIVATIVE;

ARTICLE; CALCULATION; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; STATISTICAL ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0034599368     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000403)6:7<1214::AID-CHEM1214>3.3.CO;2-A     Document Type: Article

References (71)

1. a) J. P. Collman, Acc. Chem. Res. 1977, 10, 265-272;
2. b) J. P. Collman, L. Fu, Acc. Chem. Res. 1999, 32, 455-463.
3. a) R. D. Jones, D. A. Summerville, F. Basolo, Chem. Rev. 1979, 79, 139-179;
4. b) J. E. Baldwin, P. Perlmutter in Topics in Current Chemistry (Ed.: F. L. Boschke), Springer, Berlin, 1984, p. 181;
5. c) M. Momenteau, Pure Appl. Chem. 1986, 58, 1493-1502;
6. d) Cytochrome P-450 (Ed.: P. R. Ortiz), Plenum, New York, 1986;
7. e) Metalloporphyrins in Catalytic Oxidations (Ed.: R. A. Sheldon), M. Dekker, New York, 1994;
8. f) B. Meunier, Chem. Rev. 1992, 92, 1411-1452.
9. a) H.-A. Wagenknecht, W.-D. Woggon, Angew. Chem. 1997, 109, 404-407; Angew. Chem. Int. Ed. Engl. 1997, 36, 390-392;
10. a) H.-A. Wagenknecht, W.-D. Woggon, Angew. Chem. 1997, 109, 404-407; Angew. Chem. Int. Ed. Engl. 1997, 36, 390-392;
11. b) T. Komatsu, K. Nakao, H. Nishide, E. Tsuchida, J. Chem. Soc. Chem. Commun. 1993, 728-730.
12. a) M. Komatsu, T. Aida, S. Inoue, J. Am. Chem. Soc. 1991, 113, 8492-8498;
13. b) K. S. Suslick in Comprehensive Supramolecular Chemistry, Vol. 5 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle), Pergamon, New York, 1996, p. 41;
14. c) T. Kodadek, L. A. Campbell, J. Mol. Catal. A 1996, 113, 293-310.
15. a) Y. Naruta, N. Ishihara, F. Tani, K. Maruyama, Chem. Lett. 1991, 1933-1936;
16. b) K. Konishi, K. Oda, K. Nishida, T. Aida, S. Inoue, J. Am. Chem. Soc. 1992, 114, 1313-1317.
17. a) Y. Naruta in Metalloporphyrins in Catalytic Oxidations (Ed.: R. A. Sheldon), M. Dekker, New York, 1994, p. 241-259;
18. b) E. N. Jacobsen in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, pp. 159-202.
19. a) R. L. Halterman, S.-T. Jan, J. Org. Chem. 1991, 56, 5253-5254;
20. b) J. Barry, T. Kodadek, Tetrahedron Lett. 1994, 35, 2465-2468;
21. c) J. T. Groves, P. Viski, J. Org. Chem. 1990, 55, 3628-3634.
22. a) B. Bhyrappa, G. Vaijayanthimala, K. S. Suslick, J. Am. Chem. Soc. 1999, 121, 262-263;
23. b) Y. Kuroda, Y. Kato, T. Higashioji, J. Hasegawa, S. Kawanami, M. Takahashi, N. Shiraishi, K. Tanabe, H. Ogoshi, J. Am. Chem. Soc. 1995, 117, 10950-10958;
24. c) T. Mizutani, T. Ema, T. Tomita, Y. Kuroda, H. Ogoshi, J. Am. Chem. Soc. 1994, 116, 4240-4250.
25. a) K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344;
26. b) B. R. Cook, T. J. Reinert, K. S. Suslick, J. Am. Chem. Soc. 1986, 108, 7281-7286.
27. See for example: a) J. P. Collman, Z. Wang, Chem. Tracts 1999, 12, 229-263; b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169-3172; Angew. Chem. Int. Ed. 1998, 37, 3020-3023; for exceptions see c) J. P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval, F. C. Anson, J. Am. Chem. Soc. 1980, 102, 6027; d) J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89; e) G. M. Dubowchik, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1987, 293; f) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1988, 692.
28. See for example: a) J. P. Collman, Z. Wang, Chem. Tracts 1999, 12, 229-263; b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169-3172; Angew. Chem. Int. Ed. 1998, 37, 3020-3023; for exceptions see c) J. P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval, F. C. Anson, J. Am. Chem. Soc. 1980, 102, 6027; d) J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89; e) G. M. Dubowchik, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1987, 293; f) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1988, 692.
29. See for example: a) J. P. Collman, Z. Wang, Chem. Tracts 1999, 12, 229-263; b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169-3172; Angew. Chem. Int. Ed. 1998, 37, 3020-3023; for exceptions see c) J. P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval, F. C. Anson, J. Am. Chem. Soc. 1980, 102, 6027; d) J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89; e) G. M. Dubowchik, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1987, 293; f) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1988, 692.
30. See for example: a) J. P. Collman, Z. Wang, Chem. Tracts 1999, 12, 229-263; b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169-3172; Angew. Chem. Int. Ed. 1998, 37, 3020-3023; for exceptions see c) J. P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval, F. C. Anson, J. Am. Chem. Soc. 1980, 102, 6027; d) J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89; e) G. M. Dubowchik, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1987, 293; f) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1988, 692.
31. See for example: a) J. P. Collman, Z. Wang, Chem. Tracts 1999, 12, 229-263; b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169-3172; Angew. Chem. Int. Ed. 1998, 37, 3020-3023; for exceptions see c) J. P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval, F. C. Anson, J. Am. Chem. Soc. 1980, 102, 6027; d) J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89; e) G. M. Dubowchik, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1987, 293; f) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1988, 692.
32. See for example: a) J. P. Collman, Z. Wang, Chem. Tracts 1999, 12, 229-263; b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169-3172; Angew. Chem. Int. Ed. 1998, 37, 3020-3023; for exceptions see c) J. P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval, F. C. Anson, J. Am. Chem. Soc. 1980, 102, 6027; d) J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89; e) G. M. Dubowchik, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1987, 293; f) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1988, 692.
33. See for example: a) J. P. Collman, Z. Wang, Chem. Tracts 1999, 12, 229-263; b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169-3172; Angew. Chem. Int. Ed. 1998, 37, 3020-3023; for exceptions see c) J. P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval, F. C. Anson, J. Am. Chem. Soc. 1980, 102, 6027; d) J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89; e) G. M. Dubowchik, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1987, 293; f) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1988, 692.
34. See for example: a) J. P. Collman, Z. Wang, Chem. Tracts 1999, 12, 229-263; b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169-3172; Angew. Chem. Int. Ed. 1998, 37, 3020-3023; for exceptions see c) J. P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval, F. C. Anson, J. Am. Chem. Soc. 1980, 102, 6027; d) J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89; e) G. M. Dubowchik, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1987, 293; f) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1988, 692.
35. Y. Ramondenc, R. Schwenninger, T. Phan, K. Gruber, C. Kratky, B. Kräutler, Angew. Chem. 1994, 106, 939-941; Angew. Chem. Int. Ed. Engl. 1994, 33, 889-891.
36. Y. Ramondenc, R. Schwenninger, T. Phan, K. Gruber, C. Kratky, B. Kräutler, Angew. Chem. 1994, 106, 939-941; Angew. Chem. Int. Ed. Engl. 1994, 33, 889-891.
37. a) D. J. Cram, J. M. Cram, Container Molecules and Their Guests, R. Soc. Chem. London, 1994;
38. b) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 383-395.
39. a) Reviewed in: H. Hopf, B. Witulski, Pure Appl. Chem. 1993, 65, 47-56;
40. b) for a recent application see for exapmle: F.-G. Klärner, R. Ehrhardt, H. Bandmann, R. Boese, D. Bläser, K. N. Houk, B. R. Beno, Chem. Eur. J. 1999, 5, 2119-2132;
41. c) C. D. Weiss, J. Org. Chem. 1962, 28, 74.
42. a) D. O. Cheng, E. le Goff, Tetrahedron Lett. 1977, 1469;
43. b) A. Treibs, N. Häberle, Justus Liehigs Ann. Chem. 1968, 778, 183.
44. a) J. P. Vigneron, M. Dhaemens, A. Horeau, Tetrahedron 1973, 29, 1055;
45. b) V. Rautenstrauch, Bull. Soc. Chim. Fr. 1994, 131, 515-524.
46. L. A. Paquette in Asymmetric Synthesis, Vol. 3B (Ed.: J. D. Morrison), Academic Press, New York, 1984, chap. 7.
47. R. Schwenninger, J. Schlögl, R. Konrat, B. Kräutler, unpublished results.
48. P. P. Fu, R. G. Harvey, J. Org. Chem. 1977, 42, 2407-2410.
49. K. Furuta, K. Iwanaga, H. Yamamoto, Tetrahedron Lett. 1986, 27, 4507-4510.
50. a) S. Hagishita, K. Kuriyama, Tetrahedron 1972, 28, 1435-1467;
51. b) N. Harada, K. Nakanishi, Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, California, 1983.
52. a) M. A. Petti, T. J. Shepodd, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1988, 110, 6825-6840;
53. b) P. C. Kearney, L. S. Mizoue, R. A. Kumpf, J. E. Forman, A. McCurdy, D. A. Dougherty, J. Am. Chem. Soc. 1993, 115, 9907-9919;
54. c) J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228.
55. a) Z. Li, A. Werner, K. Schlögl, Monatsh. Chem. 1993, 124, 441-452;
56. b) M. J. Brienne, J. Jaques, Bull, Soc. Chim. Fr. 1974, 2647-2652.
57. a) V. Prelog, Helv. Chim. Acta 1953, 36, 308-319;
58. b) G. M. Reisner, I. Bernal, H. Brunner, M. Muschiol, Inorg. Chem. 1978, 17, 783-789.
59. The stereogenic centers in 2 and 3 are either of S,S or of R,R configuration; a single stereochemical descriptor is used (S or R) in the text for either enantiomer of 2 or 3 (or for the pyrrolic building block of the porphyrins).
60. Handbook of Chemistry and Physics, 35th ed. (Ed.: R. C. Weast), The Chemical Rubber Co., Cleveland, 1972, p. B248.
61. The statistical incorporation of pyrroles during tetramerizing condensation reactions has been observed previously; see for example: a) D. Mauzerall, J. Am. Chem. Soc. 1960, 80, 2601-2605; b) A. Eschenmoser, Angew. Chem. 1988, 100, 5-40; Angew. Chem. Int. Ed. Engl. 1988, 27, 5-40.
62. The statistical incorporation of pyrroles during tetramerizing condensation reactions has been observed previously; see for example: a) D. Mauzerall, J. Am. Chem. Soc. 1960, 80, 2601-2605; b) A. Eschenmoser, Angew. Chem. 1988, 100, 5-40; Angew. Chem. Int. Ed. Engl. 1988, 27, 5-40.
63. The statistical incorporation of pyrroles during tetramerizing condensation reactions has been observed previously; see for example: a) D. Mauzerall, J. Am. Chem. Soc. 1960, 80, 2601-2605; b) A. Eschenmoser, Angew. Chem. 1988, 100, 5-40; Angew. Chem. Int. Ed. Engl. 1988, 27, 5-40.
64. M. J. Brienne, J. Jaques, Bull. Soc. Chim. Fr. 1973, 190-197.
65. J. Tanaka, C. Katayama, F. Ogura, H. Tatemitsu, M. Nakagawa, J. Chem. Soc. Chem. Commun. 1993, 21-22.
66. G. A. Crispino, P. T. Ho, K. B. Sharpless, Science 1993, 259, 64-66.
67. J. R. Falck, B. Mekonnen, J. Yu, J.-Y. Lai, J. Am. Chem. Soc. 1996, 118, 6096-6097.
68. See for example: P. Schreier, A. Bernreuther, M. Huffer, Analysis of Chiral Compounds (Ed.: W. de Gruyter), Berlin, 1995, p. 42 ff.
69. G. M. Sheldrick, SHELXS-86: Program for Crystal Structure Solutions, Göttingen, 1986.
70. G. M. Sheldrick, SHELXL-93: Program for the Refinement of Crystal Structures, Göttingen, 1993.
71. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-135483 (5), CCDC-135484 (6), and CCDC-135485 (7). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax; (+44)1223 336-033; e-mail: deposit@ccdc.cam.ac.uk).