"Hexacarboxytrindanes": Benzene rings with homotopic faces as scaffolds for the construction of D3 chiral architectures

Angewandte Chemie - International Edition

Volumn 44, Issue 45, 2005, Pages 7435-7439

  Borsato, Giuseppe ^a   Crisma, Marco ^b   De Lucchi, Ottorino ^a   Lucchini, Vittorio ^a   Zambon, Alfonso ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^b CNR   (Italy)

Author keywords

Chirality; Epimerization; Homotopy; NMR spectroscopy; Symmetry

Indexed keywords

CRYSTAL SYMMETRY; ESTERIFICATION; MACROMOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMODYNAMICS;

CHIRALITY; EPIMERIZATION; HOMOTOPY; SYMMETRY;

BENZENE;

EID: 28044464284     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502262     Document Type: Article

References (49)

1. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
2. J. K. Whitesell, Chem. Rev. 1989, 89, 1581.
3. a) R. Noyori, Angew. Chem. 2002, 114, 2108;
4. Angew. Chem. Int. Ed. 2002, 41, 2008;
5. b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
6. C. Moberg, Angew. Chem. 1998, 110, 260;
7. Angew. Chem. Int. Ed. 1998, 37, 248.
8. a) M. Farina, Tetrahedron Lett. 1963, 4, 2097;
9. b) M. Farina, G. Audisio, Tetrahedron 1967, 1285;
10. c) M. Farina, G. Audisio, Tetrahedron Lett. 1970, 1827;
11. d) M. Farina, G. Audisio, Tetrahedron 1970, 1839.
12. a) G. R. Underwood, B. Ramamoorthy, Tetrahedron Lett. 1970, 4125;
13. b) G. Helmchen, G. Staiger, Angew. Chem. 1977, 89, 119;
14. Angew. Chem. Int. Ed. Engl. 1977, 16, 116;
15. c) P. E. Eaton, B. Leipzig, J. Org. Chem. 1978, 43, 2483;
16. d) M. Nakazaki, K. Naemura, N. Arashiba, J. Org. Chem. 1978, 43, 689.
17. a) J. Cancelli, A. Collet, G. Gottarelli, P. Palmieri, J. Am. Chem. Soc. 1987, 109, 6454;
18. b) D. J. Cram, M. E. Tanner, S. J. Keipert, C. B. Knobler, J. Am. Chem. Soc. 1991, 113, 8909;
19. c) D. J. Cram, Nature 1992, 356, 29.
20. a) E. P. Kyba, G. W. Gokel, F. de Jong, K. Konga, L. R. Sousa, M. G. Siegel, L. Kaplan, G. D. Y. Sogah, D. J. Cram, J. Org. Chem. 1977, 42, 4173;
21. b) J. M. Lehn, P. Vierling, R. C. Hayward, J. Chem. Soc. Chem. Commun. 1979, 296;
22. c) H. Löhr, F. Vögtle, Acc. Chem. Res. 1985, 18, 65;
23. d) J. Crosby, J. F. Stoddart, X. Sun, M. R. W. Venner, Synthesis 1993, 141;
24. e) A. Gypser, D. Michel, D. S. Nirschl, K. B. Sharpless, J. Org. Chem. 1998, 63, 7322;
25. f) M. Ricci, D. Pasini, Org. Biomol. Chem. 2003, 1, 3261.
26. a) G. Schick, M. Levitus, L. Kvetko, B. A. Johnson, I. Lamparth, R. Lunkwitz, B. Ma, S. I. Kahn, M. A. Garcia-Garibay, Y. Rubin, J. Am. Chem. Soc. 1999, 121, 3246;
27. b) A. A. Goryunkov, V. Y. Marcov, I. N. Ioffe, R. D. Bolskar, M. D. Diener, I. V. Kovyuchko, S. H. Strauss, O. V. Boltalina, Angew. Chem. 2004, 116, 1015;
28. Angew. Chem. Int. Ed. 2004, 43, 997.
29. a) A. Freer, C. J. Gilmore, D. D. MacNicol, S. Swanson, Tetrahedron Lett. 1980, 21, 205;
30. b) R. J. Kaufman, R. S. Sidhu, J. Org. Chem. 1982, 47, 4941;
31. c) N. Yamasaki, Y. Inoue, T. Yokoyama, A. Tai, A. Ishida, S. Takamuku, J. Am. Chem. Soc. 1991, 113, 1933;
32. d) A. J. Wilson, M. Masuda, R. P. Sijbesma, E. W. Meijer, Angew. Chem. 2005, 117, 2315;
33. Angew. Chem. Int. Ed. 2005, 44, 2275.
34. G. Borsato, S. Brussolo, M. Crisma, O. De Lucchi, V. Lucchini, A. Zambon, Synlett 2005, 1125.
35. a) P. H. J. Carlsen, T. Katsuki, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936;
36. b) F. A. Khan, B. Prabhudas, J. Dash, N. Sahu, J. Am. Chem. Soc. 2000, 122, 9558.
37. G. Nagendrappa, H. Griesbaum, J. Agric. Food Chem. 1978, 26, 581.
38. a) K. Somekawa, M. Nomura, S. Aoki, S. Noma, T. Shimo, Org. Prep. Proced. Int. 1993, 25, 449;
39. b) I. Michieletto, F. Fabris, O. De Lucchi, Tetrahedron: Asymmetry 1999, 10, 2505.
40. 3-(S)-6: A (H2′) = 1027.8 ± 0.1 Hz (at 400 MHz), X (H1′ and H3′) = 1766.7 ± 0.1 Hz, J(AA′) = -12.5 ± 0.1 Hz, J(XX′) = 0 Hz, J(AX) = J(A′X′) = 7.6 ± 0.2 Hz, J(AX′) = J(A′X) = 6.3 ± 0.2 Hz. LAOCOON program: A. A. Bothner-by, S. Castellano, J. Chem. Phys. 1964, 41, 3863.
41. -3. CCDC-272639 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. SIR 2004 program: M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 2005, 38, 381;
42. SHELXL97 program: G. M. Sheldrick et al., SHELXL 97, Program for Crystal Structure Refinement, University of Göttingen, Göttingen, 1997.
43. P. C. Meltzer, P. Wang, P. Blundell, B. K. Madras, J. Med. Chem. 2003, 46, 1538.
44. S. M. Grayson, J. M. J. Fréchet, Chem. Rev. 2001, 101, 3819.
45. C. Nuckolls, Angew. Chem. 2004, 116, 5562;
46. Angew. Chem. Int. Ed. 2004, 43, 5456.
47. a) L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071;
48. b) J. van Gestel, A. R. A. Palmans, B. Titulaer, J. A. J. M. Vekemans, E. W. Meijer, J. Am. Chem. Soc. 2005, 127, 5490.
49. H. Choi, Y. S. Park, S. H. Yun, H. Kim, C. S. Cho, K. Ko, K. H. Ahn, Org. Lett. 2002, 4, 795.