Controlling axial conformation in 2-Arylpyridines and 1-Arylisoquinolines: Application to the asymmetric synthesis of QUINAP by dynamic thermodynamic resolution

Journal of the American Chemical Society

Volumn 131, Issue 14, 2009, Pages 5331-5343

  Clayden, Jonathan ^a   Fletcher, Stephen P ^a   McDouall, Joseph J W ^a   Rowbottom, Stephen J M ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; ATROPISOMERS; BIARYLS; BIPHENYL COMPOUNDS; CD SPECTRA; CONFORMATIONAL PREFERENCES; DYNAMIC RESOLUTION; THERMODYNAMIC CONTROL;

CHELATION; CONFORMATIONS; ELECTRON TRANSITIONS; THERMODYNAMICS;

COMPLEXATION;

ISOQUINOLINE DERIVATIVE; LIGAND; PYRIDINE DERIVATIVE; SULFOXIDE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFORMATION; HEATING; ISOMER; SUBSTITUTION REACTION; SYNTHESIS; THERMODYNAMICS;

EID: 67749093252     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900722q     Document Type: Article

References (90)

1. Hoffmann, R. W. Angew. Chem., Int. Ed. 2000, 39, 2054-2070.
2. Betson, M. S.; Bracegirdle, A.; Clayden, J.; Helliwell, M.; Lund, A.; Pickworth, M.; Snape, T. J.; Worrall, C. P. Chem. Commun. 2007, 754-756.
3. (a) Stenkamp, D.; Hoffmann, R. W.; Göttlich, R. Eur. J. Org. Chem. 1999, 2929-2936.
4. (b) Hoffmann, R. W.; Stahl, M.; Schopfer, U.; Frenking, G. Chem.-Eur. J. 1998, 4, 559-566.
5. (c) Yamamoto, Y.; Kin, H.; Suzuki, I.; Asao, N. Tetrahedron Lett. 1996, 37, 1863.
6. (d) Alder, R. W.; Anderson, K. R.; Benjes, P. A.; Butts, C. P.; Koutentis, P. A.; Orpen, A. G. Chem. Commun. 1998, 309-310.
7. (e) O'Hagan, D.; Rzepa, H. S.; Schüler, M.; Slawin, A. M. Z. Beilstein J. Org. Chem. 2006, 2, No. 19.
8. (a) Mikami, K.; Shimizu, M.; Zhang, H.-C.; Maryanoff, B. E. Tetrahedron 2001, 57, 2917-2951.
9. (b) Clayden, J.; Vassiliou, N. Org. Biomol. Chem. 2006, 4, 2667-2678.
10. (c) Noe, C. R.; Knollmüller, M.; Ettmayer, P. Angew. Chem., Int. Ed. 1988, 27, 1379-1381.
11. (a) Clayden, J.; Lund, A.; Vallverdu', L.; Helliwell, M. Nature (London) 2004, 431, 966-971.
12. (b) Clayden, J.; Vallverdu', L.; Helliwell, M. Chem. Commun. 2007, 2357-2359.
13. (c) Clayden, J.; Kenworthy, M. N.; Youssef, L. H. Tetrahedron Lett. 2000, 41, 5171-5175.
14. (d) Clayden, J.; Lund, A.; Youssef, L. H. Org. Lett. 2001, 3, 4133-4136.
15. (e) Clayden, J.; Pink, J. H.; Yasin, S. A. Tetrahedron Lett. 1998, 39, 105- 108.
16. (f) Clayden, J.; Westlund, N.; Frampton, C. S.; Helliwell, M. Org. Biomol. Chem. 2006, 4, 455-461.
17. (f) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 3331-3334.
18. (a) Clayden, J. Chem. Commun. 2004, 127.
19. (b) Betson, M. S.; Clayden, J.; Helliwell, M.; Johnson, P.; Lai, L. W.; Pink, J. H.; Stimson, C. C.; Vassiliou, N.; Westlund, N.; Yasin, S. A.; Youssef, L. H. Org. Biomol. Chem. 2006, 4, 424-443.
20. Betson, M. S.; Clayden, J.; Helliwell, M.; Mitjans, D. Org. Biomol. Chem. 2005, 3, 3898-3904.
21. (a) Clayden, J.; Foricher, Y. J. Y.; Helliwell, M.; Johnson, P.; Mitjans, D.; Vinader, V. Org. Biomol. Chem. 2006, 4, 444-454.
22. (b) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695- 698.
23. (a) Betson, M. S.; Clayden, J.; Lam, H. K.; Helliwell, M. Angew. Chem., Int. Ed. 2005, 44, 1241-1244.
24. (b) Clayden, J.; Vallverdu', L.; Clayton, J.; Helliwell, M. Chem. Commun. 2008, 561-563.
25. (c) Clayden, J.; Lemiégre, L.; Pickworth, M.; Jones, L. Org. Biomol. Chem. 2008, 6, 2908-2913.
26. (d) Clayden, J.; Vallverdu', L.; Helliwell, M. Org. Biomol. Chem. 2006, 4, 2106-2118.
27. (a) Beak, P.; Anderson, D. R.; Curtis, M. D.; Laumer, J. M.; Pippel, D. J.; Weisenburger, G. A. Acc. Chem. Res. 2000, 33, 715-727.
28. (b) Lee, W. K.; Park, Y. S.; Beak, P. Acc. Chem. Res. 2009, 42, 224- 234.
29. Clayden, J.; Mitjans, D.; Youssef, L. H. J. Am. Chem. Soc. 2002, 124, 5266-5267.
30. (a) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron 2004, 60, 4399- 4412.
31. (b) Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556-2558.
32. (c) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163-3166.
33. Clayden, J.; Kubinski, P. M.; Sammiceli, F.; Helliwell, M.; Diorazio, L. Tetrahedron 2004, 60, 4387-4397.
34. Clayden, J.; Worrall, C. P.; Moran, W.; Helliwell, M. Angew. Chem., Int. Ed. 2008, 47, 3234-3237.
35. (a) Guiry, P. J.; Saunders, C. P. Adv. Synth. Catal. 2004, 346, 497- 537.
36. (b) Chelucci, G.; Orru, G.; Pinna, G. A. Tetrahedron 2003, 59, 9471-9515.
37. (c) Trudeau, S.; Morgan, J. B.; Shrestha, M.; Morgan, J. P. J. Org. Chem. 2005, 70, 9538-9544.
38. (d) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506.
39. (e) Faller, J. W.; Grimmond, B. J. Organometallics 2001, 20, 2454-2458.
40. (f) Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174- 10175.
41. (g) Li, X.; Kong, L.; Gao, Y.; Wang, X. Tetrahedron Lett. 2007, 48, 3915-3917.
42. (h) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535-2538.
43. (i) Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem.-Eur. J. 2003, 9, 2797-2811.
44. (j) Gommermann, N.; Knochel, P. Tetrahedron 2005, 61, 11418-11426.
45. Lim, C. W.; Tissot, O.; Mattison, A.; Hooper, M. W.; Brown, J. M.; Cowley, A. R.; Hulmes, D. I.; Blacker, A. J. Org. Proc. Res. Dev. 2003, 7, 379-384.
46. Schlosser, M.; Cottet, F. Eur. J. Org. Chem. 2002, 4181-4184.
47. Kang, H.; Facchetti, A.; Stern, C. L.; Rheingold, A. L.; Kassel, W. S.; Marks, T. J. Org. Lett. 2005, 7, 3721-3724.
48. Thaler, T.; Geittner, F.; Knochel, P. Synlett 2007, 2655-2657.
49. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, 2002.
50. Adams, R.; Yuan, H. C. Chem. Rev. 1933, 12, 261-338.
51. (a) Wolf, C. Dynamic Stereochemistry of Chiral Compounds; Royal Society of Chemistry: Cambridge, 2008.
52. (b) Bott, G.; Field, L. D.; Sternhell, S. J. Am. Chem. Soc. 1980, 102, 5618-5626.
53. (a) Baker, R. W.; Rea, S. O.; Sargent, M. V.; Schenkelaars, E. M. C.; Tjahjandarie, T. S.; Totaro, A. Tetrahedron 2005, 61, 3733-3743.
54. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis 1999, 429-434.
55. (c) Tucker, S. C.; Brown, J. M.; Oakes, J.; Thornthwaite, D. Tetrahedron 2001, 57, 2545-2554.
56. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
57. (a) Solladie', G.; Hutt, J.; Girardin, A. Synlett 1987, 173-173.
58. (b) Andersen, K. K. Tetrahedron Lett. 1962, 93-95.
59. Concurrently with our work, Knochel reported the use of sulfoxides for the synthesis of QUINAP by classical resolution; see ref 19.
60. The X-day crystallographic data for (R,P)-13 has been deposited with the Cambridge Crystallographic Database, deposition number 716802.
61. Davies, M. W.; Shipman, M.; Tucker, J. H. R.; Walsh, T. R. J. Am. Chem. Soc. 2006, 128, 14260-14260.
62. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian Inc.: Wallingford, CT, 2004.
63. Oki, M. Top. Stereochem. 1983, 14, 1.
64. Clayden, J.; Fletcher, S. P.; Rowbottom, S. J. M.; Helliwell, M. Cambridge Crystallographic Database, deposition number 703502.
65. Berova, N.; Di Bari, L.; Pescitelli, G. Chem. Soc. Rev. 2007, 36, 914- 931.
66. (a) Holzwarth, G.; Doty, P. J. Am. Chem. Soc. 1965, 87, 218.
67. (b) Greenfield, N.; Fasman, G. D. Biochemistry 1969, 8, 4108-4116.
68. (c) Greenfield, N. J. Anal. Biochem. 1996, 235, 1-81.
69. (a) Mason, S. F.; Seal, R. H.; Roberts, D. R. Tetrahedron 1974, 30, 1671-1682.
70. (b) Bari, B. D.; Pescitelli, G.; Salvadori, P. J. Am. Chem. Soc. 1999, 121, 7998-8004.
71. (c) Gawroñski, J.; Grycz, P.; Kwit, M.; Rychlewska, U. Chem.-Eur. J. 2002, 8, 4210-4215.
72. (d) Tartaglia, S.; Padula, D.; Scafato, P.; Chiummiento, L.; Rosini, C. J. Org. Chem. 2008, 73, 4865-4873, and references therein.
73. (a) Diedrich, C.; Grimme, S. J. Phys. Chem. A. 2003, 107, 2524- 2539.
74. (b) Mori, T.; Inoue, Y.; Grimme, S. J. Phys. Chem. A. 2007, 111, 4222-4234.
75. For examples, see: (a) Bringmann, G.; Gulder, T. A. M.; Reichert, M; Gulder, T. Chirality 2008, 20, 628-642.
76. (b) Furche, F; Ahlrichs, R.; Wachsmann, C.; Weber, E.; Sobanski, A.; Vögtle, F.; Grimme, S. J. Am. Chem. Soc. 2000, 122, 1717-1724.
77. (c) Kondru, R. K.; Wipf, P.; Beratan, D. N. J. Am. Chem. Soc. 1998, 120, 2204-2205.
78. (d) Gawronski, J. K.; Kwit, M.; Boyd, D. R.; Sharma, N. D.; Malone, J. F.; Drake, A. F. J. Am. Chem. Soc. 2005, 127, 4308-4319.
79. (e) Bringmann, G.; Maksimenka, K.; Mutanyatta-Comar, J.; Knauer, M.; Bruhn, T. Tetrahedron 2007, 63, 9810-9824.
80. (f) Schlingmann, G.; Taniguchi, T.; He, H.; Bigelis, R.; Yang, H. Y.; Koehn, F. E.; Carter, G. T.; Berova, N. J. Nat. Prod. 2007, 70, 1180-1187.
81. (g) Bracher, F.; Eisenreich, W. J.; Mühlbacher, J.; Dreyer, M.; Bringmann, G. J. Org. Chem. 2004, 69, 8602-8608.
82. (h) Mori, T.; Grimme, S.; Inoue, Y. J. Org. Chem. 2007, 72, 6998-7010. (I) Mori, T.; Inoue, Y.; Grimme, S. J. Phys. Chem. A. 2007, 111, 7955-8006.
83. http://www.ipc.uni-karlsruhe.de/tch/tch1/TBL/tbl.html
84. For the use of such "molecular brakes", see: (a) Kottas, G. S.; Clarke, L. I.; Horinek, D.; Michl, J. Chem. Rev. 2005, 105, 1281-1376.
85. (b) Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191.
86. Feringa, B. L. Molecular Switches; Wiley-VCH: Weinheim, 1995.
87. Knöpfel, T. E.; Aschwanden, P.; Ichikawa, T.; Watanabe, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2004, 43, 5971-5973.
88. For the asymmetric synthesis of aryl-pyridines using a sulfinyl group to induce asymmetry under kinetic control, see ref 23. For other methods, see: (a) Kakiuchi, F.; Le Gendre, P.; Yamada, A.; Ohtaki, H.; Murai, S. Tetrahedron Asymmetry 2000, 11, 2647.
89. (b) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem. 2004, 116, 3795-3797.
90. It is in fact possible to re-isolate and recycle (by further equilibration) the minor, less stable diastereoisomer of 13 in low yield (ca 12%) after this equilibration: yields are limited by the instability of 13 on silica. Higher yields were obtained by Knochel et al. (ref 19) employing Florisil, but our equilibration method is particularly suitable for use on large scale, where the expense of Florisil becomes prohibitive.