Atropisomerism at C - S bonds: Asymmetric synthesis of diaryl sulfones by dynamic resolution under thermodynamic control

Angewandte Chemie - International Edition

Volumn 48, Issue 34, 2009, Pages 6270-6273

  Clayden, Jonathan ^a   Senior, James ^a   Helliwell, Madeleine ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Atropisomerism; Dynamic resolution; Rotational barriers; Sulfones; Sulfoxides

Indexed keywords

ATROPISOMERISM; DYNAMIC RESOLUTION; ROTATIONAL BARRIERS; SULFONES; SULFOXIDES;

THERMODYNAMICS;

SULFONE; SULFOXIDE;

ARTICLE; CHEMISTRY; CONFORMATION; ISOMERISM; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ISOMERISM; MOLECULAR CONFORMATION; SULFONES; SULFOXIDES; THERMODYNAMICS;

EID: 70349933112     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901718     Document Type: Article

References (70)

1. G. Bringmann, A. J. P. Mortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518;
2. Angew. Chem. Int. Ed. 2005, 44, 5384.
3. M. Berthod, G. Mignani, G. Woodward, M. Lemaire, Chem. Rev. 2005, 105, 1801.
4. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
5. 3 atropisomers, see: S. Murrison, D. Glowacki, C. Einzinger, J. Titchmarsh, S. Bartlett, B. McKeever-Abbas, S. Warriner, A. Nelson, Chem. Eur. J. 2009, 15, 2185, and references therein.
6. a) R. Actams, H. C. Yuan, Chem. Rev. 1933, 12, 261;
7. b) T. W. Wallace, Org. Biomol. Chem. 2006, 4, 3197, and references therein.
8. a) J. Clayden, Angew. Chem. 1997, 109, 986;
9. Angew. Chem. Int. Ed. Engl. 1997, 36, 949;
10. J. Clayden, D. Mitjans, L. H. Youssef, J. Am. Chem. Soc. 2002, 124, 5266;
11. J. Clayden, Chem. Commun. 2004, 127;
12. b) D. J. Bennett, A. J. Blake, P. A. Cooke, C. R. A. Godfrey, P. L. Pickering, N. S. Simpkins, M. D. Walker, C. Wilson, Tetrahedron 2004, 60, 4491;
13. O. Kitagawa, M. Yoshikawa, H. Tamnabe, T. Morita, M. Takahashi, Y. Dobashi, T. Taguchi, J. Am. Chem. Soc. 2006, 128, 12923, and references therein;
14. c) J. Clayden, H. Turner, M. Helliwell, E. Moir, J. Org. Chem. 2008, 73, 4415;
15. d) J. Clayden, A. Lund, L. Vallverdú, M. Helliwell, Nature 2004, 431, 966;
16. J. Clayden, L. Vallverdú, M. Helliwell, Chem. Commun. 2007, 2357;
17. J. Clayden, C. McCarthy, M. Helliwell, Chem. Commun. 1999, 2059;
18. e) J. Clayden, L. Vallverdú, J. Clayton, M. Helliwell, Chem. Commun. 2008, 561;
19. R. A. Bragg, J. Clayden, G. A. Morris, J. H. Pink, Chem. Eur. J. 2002, 8, 1279;
20. J. Clayden, J. H. Pink, Angew. Chem. 1998, 110, 2040;
21. Angew. Chem. Int. Ed. 1998, 37, 1937;
22. f) J. Clayden, M. Helliwell, J. H. Pink, N. Westlund, J. Am. Chem. Soc. 2001, 123, 12449;
23. J. Clayden, J. H. Pink, Tetrahedron Lett. 1997, 38, 2561;
24. J. Clayden, J. H. Pink, Tetrahedron Lett. 1997, 38, 2565;
25. g) Y. Chen, M. D. Smith, K. D. Shimizu, Tetrahedron Lett. 2001, 42, 7185;
26. W.-M. Dai, Y. Li, Y. Zhang, Z. Yue, J. H. Wu, Chem. Eur. J. 2008, 14, 5538, and references therein;
27. S. Brandes, B. M. Kjaersgaard, K. A. Jørgensen, Angew. Chem. 2006, 118, 1165;
28. Angew. Chem. Int. Ed. 2006, 45, 1147;
29. J. Clayden, P. Johnson, J. H. Pink, M. Helliwell, J. Org. Chem. 2000, 65, 7033;
30. J. Clayden, M. Helliwell, C. McCarthy, N. Westlund, J. Chem. Soc. Perkin Trans. 1 2000, 3232;
31. h) see for example P. Eveleigh, E. C. Hulme, C. Schudt, N. J. M. Birdsall, Mol. Pharmacol. 1989, 35, 477;
32. S. D. Guile, J. R. Bantick, M. E. Cooper, D. K. Donald, C. Eyssade, A. H. Ingall, R. J. Lewis, B. P. Martin, R. T. Mohammed, T. J. Potter, R. H. Reynolds, S. A. St-Gallay, A. D Wright, J. Med. Chem. 2007, 50, 254;
33. A. Palani, S. Shapiro, J. W. Clader, W. J. Greenlee, D. Blythin, K. Cox, N. E. Wagner, J. Strizki, B. M. Baroudy, N. Dan, Bioorg. Med. Chem. Lett. 2003, 13, 705.
34. a) M. S. Betson, J. Clayden, C. P. Worrall, S. Peace, Angew. Chem. 2006, 118, 5935;
35. Angew. Chem. Int. Ed. 2006, 45, 5803;
36. b) J. Clayden, C. P. Worrall, W. Moran, M. Helliwell, Angew. Chem. 2008, 120, 3278;
37. Angew. Chem. Int. Ed. 2008, 47, 3234;
38. c) Y. Koizumi, S. Suzuki, K. Takeda, K. Murahashi, M. Horikawa, K. Katagiri, H. Masu, T. Kayo, I. Azumaya, S. Fujii, T. Furuta, K. Tanaka, T. Kan, Tetrahedron: Asymmetry 2008, 19, 1407;
39. d) K. Fuji, T. Oka, T. Kawabata, T. Kinoshita, Tetrahedron Lett. 1998, 39, 1373.
40. H. Kessler, A. Rieker, W. Rundel, J. Chem. Soc. Chem. Commun. 1968, 475;
41. L. Lunazzi, A. Mazzanti, M. Minzoni, Tetrahedron 2005, 61, 6782.
42. a) W. Y. Lam, J. C. Martin, J. Org. Chem. 1981, 46, 4458;
43. b) D Casarini, L. Lunazzi, F. Gasparrini, C. Villani, M. Cirilli, J. Org. Chem. 1995, 60, 97;
44. c) D Casarini, L. Lunazzi, S. Alcaro, F. Gasparrini, C. Villani, J. Org. Chem. 1995, 60, 5515;
45. d) C. Villani, W. H. Pirkle, Tetrahedron: Asymmetry 1995, 6, 27.
46. F Y. Kwong, S. L. Buchwald, Org. Lett. 2002, 4, 3517.
47. a) C. Wolf, Dynamic Stereochemistry of Chiral Compounds, Royal Society of Chemistry, Cambridge, 2008;
48. b) O. Trapp, V. Schurig, Chirality 2002, 14, 465;
49. c) C. Wolf, Chem. Soc. Rev. 2005, 34, 595.
50. Rates of racemization of 1a, 3a, 23, and 24 were determined by observation of first-order decay to a racemic mixture (after Chromatographic resolution in the case of la and 3a) at an appropriate temperature, monitored by HPLC. The rate of racemization of 2a was determined by application of the method of Schurig and Trapp (Ref. [10b]) to the elution profile shown in Figure 1 c. Further details of kinetic parameters relating to the mechanism of racemization of these compounds will be reported in a future publication.
51. CCDC 724152 (1a), 724152, 724153 (2a), 724154 (3a), 724155(13), 724156 (14), 724158 (21), and 724159 (22) contain 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. Details of the analysis are provided in the supporting information. Crystals of sulfoxides 13, 14, and 21 were enantio-merically pure and the absolute structure parameters confirmed their absolute configurations. We were unable to obtain good-quality crystals of enantiomerically pure 22, and Figure 2 e shows a molecule of (S, P)-22 extracted from the crystal structure of (±)-22.
52. P. Beak, D. R. Anderson, M. D Curtis, J. M. Laumer, D. J. Pippel, G. A. Weisenburger, Acc. Chem. Res. 2000, 33, 715;
53. W. K. Lee, Y. S. Park, P. Beak, Acc. Chem. Res. 2009, 42, 224.
54. See references [5b, 6b] and a) J. Clayden, S. P. Fletcher, J. J. W. McDouall, S. J. M. Rowbottom, J. Am. Chem. Soc. 2009, 131, 5331;
55. b) J. Clayden, P. M. Kubinski, F. Sammiceli, M. Helliwell, L. Diorazio, Tetrahedron 2004, 60, 4387;
56. c) J. Clayden, L. W. Lai, M. Helliwell, Tetrahedron 2004, 60, 4399;
57. d) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755;
58. Angew. Chem. Int. Ed. 1999, 38, 2556;
59. e) A. Bracegirdle, J. Clayden, L. W. Lai, Beilstein J. Org. Chem. 2008, 4, 47.
60. M. Iwao, T. Iihama, K. K. Mahalanabis, H. Perrier, V. Snieckus, J. Org. Chem. 1989, 54, 24;
61. C. Quesnelle, T. Iihama, T. Aubert, H. Perrier, V. Snieckus, Tetrahedron Lett. 1992, 33, 2625;
62. J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, Oxford, 2002;
63. J. Clayden in Chemistry of Organolithium Compounds, Vol. 1 (Eds.: Z. Rappoport, I. Marek), Wiley, New York, 2004, p. 495.
64. K. K. Andersen, Tetrahedron Lett. 1962, 3, 93;
65. C. Mioskowski, G. Solladié, Tetrahedron 1980, 36, 227;
66. G. Solladié, J. Hutt, A. Girardin, Synthesis 1987, 173.
67. The configuration of the major conformer of 12 is unknown and is arbitrarily shown as (R, M).
68. In DMSO, coalescences at ca. 60°C confirmed that the spectroscopic 10:1 ratio represents a mixture of interconverting conformers. Lineshape analysis gave an approximate half-life for epimerization in DMSO for 14 of ca. 0.5 s at 25°C.
69. F. A. Davis, B. C. Chen, Chem. Rev. 1992, 92, 919. The absolute configuration of 22 was assigned by analogy with related oxidations of known aryl methyl sulfides.
70. The absolute configuration of 23 was assigned on the basis of the absolute C - S axial configuration displayed in the crystal structure of 21. The absolute configuration of 24 is based on the relative conformational preference shown in the crystal structure of (±)-22 coupled with the expected enantioselectivity of the oxidation of 19 (ref. [19]). Consistent with (though of course not proving) these assignments, both products are (P)-(-), and related atropisomeric sulfonyl ethers (ref. [6b]) are also likewise (P)-(-). For a conformational study of 1,2-bissulfones, see: J. Lacour, D. Monchaud, J. Mareda, F. Favarger, G. Bernardinelli, Helv. Chim. Acta 2003, 86, 65.