Atropisomerism, biphenyls, and fluorine: A comparison of rotational barriers and twist angles

ChemBioChem

Volumn 5, Issue 5, 2004, Pages 644-649

  Leroux, Frédéric ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Atropisomerism; Biaryls; Flourine; Rotational barriers; Twist angels

Indexed keywords

BIPHENYL; FLUORINE;

CHEMICAL BINDING; CHIRALITY; CRYSTAL STRUCTURE; FLUORINATION; ISOMERISM; MATHEMATICAL COMPUTING; PRIORITY JOURNAL; RACEMIZATION; ROOM TEMPERATURE; ROTATION; SHORT SURVEY; X RAY ANALYSIS;

AROMATASE INHIBITORS; BIPHENYL COMPOUNDS; ENZYME INHIBITORS; FLUORINE; HYDROCARBONS, FLUORINATED; ISOMERISM; MOLECULAR CONFORMATION; ROTATION; STEROID 17-ALPHA-HYDROXYLASE;

EID: 4544387720     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200300906     Document Type: Short Survey

References (78)

1. a) K. B. G. Torssell, Natural Product Chemistry, Taylor and Francis, New York, 1997;
2. b) G. Bringmann, F. Pokorny in The Alkaloids, Vol. 46 (Ed.: G. A. Cordell), Academic Press, New York, 1995, p. 127;
3. c) T. Okuda, T. Yoshida, T. Hatano in Prog. Chem. Org. Nat. Prod., Vol. 66 (Eds.: W. Herz, G. W. Kirby, R. E. Moore, W. Steglich, C. Tamm), Springer, Vienna, 1995, p. 1.
4. a) D. H. Williams, B. Bardsley, Angew. Chem. 1999, 777, 1264-1286; Angew. Chem. Int. Ed. 1999, 38, 1172-1193;
5. a) D. H. Williams, B. Bardsley, Angew. Chem. 1999, 777, 1264-1286; Angew. Chem. Int. Ed. 1999, 38, 1172-1193;
6. b) K. C. Nicolaou, C. N. C. Boddy, S. Bräse, N. Winssinger, Angew. Chem. 1999, 777, 2230-2287; Angew. Chem. Int. Ed. 1999, 38, 2096-21S2;
7. b) K. C. Nicolaou, C. N. C. Boddy, S. Bräse, N. Winssinger, Angew. Chem. 1999, 777, 2230-2287; Angew. Chem. Int. Ed. 1999, 38, 2096-21S2;
8. c) S. M. Kupchan, R. W. Britton, M. F. Ziegler, C. J. Gilmore, R. J. Restivo, R. F. Brian, J. Am. Chem. Soc. 1973, 95, 133S-1336.
9. a) C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503-517;
10. b) L. Pu, Chem. Rev. 1998, 98, 2405-2494;
11. c) K. Mikami, K. Aikawa, Y. Yusa, J. J. Jodry, M. Yamanaka, Synlett 2002, 1561-1578;
12. d) K. Mikami, M. Yamanaka, Chem. Rev. 2003, 103, 3369-3400;
13. e) P. J. Walsh, A. E. Lurain, J. Balsells, Chem. Rev. 2003, 103, 3297-3344.
14. BINAP = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl: a) R. Noyori, Angew. Chem. 2002, 774, 2108-2123; Angew. Chem. Int. Ed. 2002, 47, 2008-2022;
15. BINAP = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl: a) R. Noyori, Angew. Chem. 2002, 774, 2108-2123; Angew. Chem. Int. Ed. 2002, 47, 2008-2022;
16. b) R. Noyori, Chemtech 1992, 22, 360-367.
17. Meo-BIPHEP = 6,6′-bis(diphenylphosphanyl)-2,2′-dimethoxy-1, 1′-biphenyl: a) R. Schmid, J. Foricher, M. Cereghetti, P. Schönholzer, Helv. Chim. Acta 1991, 74, 370-389;
18. b) R. Schmid, Chimia 1996, 50, 110-113.
19. a) P. J. Collings, M. Hird, Introduction to Liquid Crystals Chemistry and Physics, Taylor and Francis, London, 1997;
20. b) J. W. Goodby, N. A. Clark, S. T. Laggerwall, Ferroelectric Liquid Crystals: Principles, Properties and Applications, Gordon and Breach, Philadelphia, 1991.
21. A. A. Patchett, R. P. Nargund, "Privileged Structures" in Topics in Drug Design and Discovery (Ed.: G. L. Trainor), Annu. Rep. Med. Chem. (Section IV) 2000, 35, 269-298.
22. a) A. Kleemann, J. Engel, Pharmaceutical Substances: Syntheses, Patents, Applications, Thieme, Stuttgart, 1999, pp. 306-307, 1116-1119, 1024-1025, and 1984-1985;
23. b) H. Ji, M. Leung, Y. Zhang, K. J. Catt, K. Sandberg, J. Biol. Chem. 1994, 269, 16533-16536;
24. c) H. T. Schambye, S. H. Hjorth, J. Weinstock, T. W. Schwartz, Mol. Pharmacol. 1995, 47, 425-431;
25. d) S. Perlman, H. T. Schambye, R. A. Rivero, W. J. Greenlee, S. A. Hjorth, T. W. Schwartz, J. Biol. Chem. 1995, 270, 1493-1496;
26. e) V. Nirula, W. Zheng, R. Sothinathan, K. Sandberg, Br. J. Pharmacol. 1996, 779, 1505-1507;
27. f) V. Nirula, W. Zheng, K. Krishnamurthi, K. Sandberg, FEBS Lett. 1996, 394, 361-364.
28. a) R. W. Hartmann, Eur. J. Pharm. Sci. 1994, 2, 15-16;
29. b) B. G. Wachall, M. Hector, Y. Zhuang, R. W. Hartmann, Bioorg. Med. Chem. 1999, 7, 1913-1924;
30. c) Y. Zhuang, B. C. Wachall, R. W. Hartmann, Bioorg. Med. Chem. 2000, 8, 1245-1252;
31. d) F. Leroux, T. Hutschenreuter, C. Charrière, R. Scopelliti, R. W. Hartmann, Helv. Chim. Acta 2003, 86, 2671-2686.
32. J. P. Van Wauve, P. A. J. Janssen, J. Med. Chem. 1989, 32, 2231-2239.
33. a) M. Schlosser, Tetrahedron 1978, 34, 3-17;
34. b) M. Schlosser, Angew. Chem. 1998, 770, 1538-1556; Angew. Chem. Int. Ed. 1998, 37, 1496-1513;
35. b) M. Schlosser, Angew. Chem. 1998, 770, 1538-1556; Angew. Chem. Int. Ed. 1998, 37, 1496-1513;
36. c) "The Chemical and Physiological Size of Fluorine" M. Schlosser in Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets (Ed.: V. A. Soloshonok), Wiley, Chichester, 1999, pp. 613-659.
37. G. H. Christie, J. Kenner, J. Chem. Soc. 1922, 121, 614-620.
38. E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, John Wiley and Sons, 1994, pp. 1142-1145.
39. F. Grein, J. Phys. Chem. A 2002, 106, 3823-3827.
40. a) A. Bondi, J. Phys. Chem. 1964, 68, 441-451;
41. b) A. Bondi, J. Phys. Chem. 1966, 70, 3006-3007.
42. G. Bott, L. D. Field, S. Sternhell, J. Am. Chem. Soc. 1980, 102, 5618-5626.
43. a) M. Charton, J. Am. Chem. Soc. 1975, 97, 1552-1556;
44. b) M. Charton, J. Am. Chem. Soc. 1975, 97, 6159-6161;
45. c) M. Charton, J. Am. Chem. Soc. 1975, 97, 6472-6473;
46. d) M. Charton, J. Org. Chem. 1976, 41, 2217-2220;
47. e) M. Charton, J. Org. Chem. 1977, 42, 2528-2529;
48. f) M. Charton, Prog. Phys. Org. Chem. 1973, 10, 81-204;
49. g) R. Gallo, Prog. Phys. Org. Chem. 1983, 14, 115-163.
50. B. E. Smart in Chemistry of Organofluorine Compounds (Ed.: M. Hudlicky), American Chemical Society, Washington DC, 1995, p. 2S.
51. Y. H. Zhao, M. H. Abraham, A. M. Zissimos, J. Org. Chem. 2003, 68, 7368-7373.
52. The author is very grateful to one of the referees for pointing out this fact.
53. M. Schlosser, D. Michel, Tetrahedron 1996, 52, 99-108.
54. a) A. Mannschreck, L. Ernst, Chem. Ber. 1971, 104, 228-247;
55. b) W. J. E. Parr, T. Schaefer, Acc. Chem. Res. 1980, 13, 400-406;
56. c) T. Schaefer, R. P. Veregin, R. Laatikainen, R. Sebastian, K. Marat, J. L. Charlton, Can. J. Chem. 1982, 60, 2611-2616.
57. a) R. Cosmo, S. Sternhell, Aust. J. Chem. 1987, 40, 35-47;
58. b) K. Mislow, M. A. W. Glass, H. B. Hopps, E. Simon, G. H. Wahl, J. Am. Chem. Soc., 1964, 86, 1710-1733;
59. c) O. Yamamoto, H. Nakanishi, Tetrahedron 1973, 29, 781-787.
60. R. Adams, H. C. Yuan, Chem. Rev. 1933, 72, 261-338.
61. T.-H. Tang, M. Nowakowska, J. E. Guillet, I. G. Csizmadia, J. Mol. Struct. 1991, 232, 133-146.
62. a) N. Hasaka, M. Okigawa, I. Kouno, N. Kawano, Bull. Chem. Soc. Jpn. 1982, 55, 3828-3830;
63. b) F. Leroux, M. Maurin, N. Nicod, R. Scopelliti, Tetrahedron Lett. 2004, 45, 1899-1902.
64. H. Jendralla, C.-h. Li, E. Paulus, Tetrahedron: Asymmetry 1994, 5, 1297-1320.
65. O. Desponds, M. Schlosser, Tetrahedron Lett. 1996, 37, 47-48.
66. C. Wolf, W. A. König, C. Rouzssel, Liebigs Ann. 1995, 781-786.
67. H. Cailleau, A. Girard, F. Moussa, C. M. E. Zeyen, Solid State Commun. 1979, 29, 259-261.
68. Rajnikant, D. Watkin, G. Trunter, Acta Crystallogr. Sect. C 1995, 51, 1452-1454.
69. B. Aldridge, G. De Luca, M. Edgar, J. W. Emsley, M. I. C. Furby, M. Webster, Liquid Cryst. 1998, 24, 569-581.
70. C. Romming, H. M. Seip, I.-M. A. Oymo, Acta Chem. Scand. Ser. A 1974, 28, 507-514.
71. D. D. MacNeil, A. Decken, Acta Crystallogr. Sect. C 1999, 55, 628-630.
72. H. Bock, M. Sievert, Z. Havlas, Chem. Eur. J. 1998, 4, 677-685.
73. A. Almenningen, O. Bastiansen, L. Fernholt, S. Gundersen, E. Kloster-Jensen, J. Mol. Struct. 1985, 728, 77-93.
74. W. B. Gleason, D. Britton, Cryst. Struct. Commun. 1976, 5, 483-488.
75. a) D. Michel, M. Schlosser, Tetrahedron 2000, 56, 4253-4260;
76. b) M. Schlosser, L. Guio, F. Leroux, J. Am. Chem. Soc. 2001, 123, 3822-3823;
77. c) B. K. Park, N. R. Kitteringham, Drug Metab. Rev. 1994, 26, 605-643.
78. R. W. Hartmann, T. Hutschenreuter, unpublished results.