Understanding the torquoselectivity in 8π-electrocyclic cascade reactions: Synthesis of fenestradienes versus cyclooctatrienes

Journal of the American Chemical Society

Volumn 131, Issue 37, 2009, Pages 13387-13398

  Hulot, Catherine ^a   Amiri, Shadi ^b   Blond, Gaëlle ^a   Schreiner, Peter R ^b   Suffert, Jean ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE REACTIONS; CONFORMATIONAL FLEXIBILITY; CYCLO-ALKANES; DENSITY FUNCTIONAL COMPUTATIONS; DIASTEREOSELECTIVITIES; ELECTROCYCLIZATION; EQUATORIAL POSITIONS; HIGHER TEMPERATURES; REACTION CONDITIONS; RING SIZES; SINGLE BOND; THERMODYNAMIC PRODUCTS; TORQUOSELECTIVITY; TRANSITION STRUCTURES; VALENCE ISOMER;

CONFORMATIONS; ISOMERS;

TOPOLOGY;

CHEMICAL COMPOUND; CYCLOOCTATRIENE; FENESTRADIENE; UNCLASSIFIED DRUG; ALKENE; ALKYNE; CYCLOOCTANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DENSITY FUNCTIONAL THEORY; HYDROGENATION; REACTOR CASCADE; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS; CHEMISTRY; CONFORMATION; ENZYME SPECIFICITY; KINETICS; QUANTUM THEORY; STEREOISOMERISM; TEMPERATURE;

ALKENES; ALKYNES; CYCLIZATION; CYCLOOCTANES; HYDROGENATION; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TEMPERATURE; THERMODYNAMICS;

EID: 70349405091     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja903914r     Document Type: Article

References (89)

1. Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 2099-2111.
2. (a) Kallel, E. A.; Wang, Y.; Spellmeyer, D. C.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 6759-6763.
3. (b) Rudolf, K.; Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 3708-3710.
4. (c) Spellmeyer, D. C.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 3412-3416.
5. Thomas, B. E.; Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 4165-4169.
6. Lecea, B.; Arrieta, A.; Cossio, F. P. J. Org. Chem. 2005, 70, 1035-1041.
7. Thomas, B. E.; Evanseck, J. D.; Houk, K. N. Isr. J. Chem. 1993, 33, 287-293.
8. Kröner, M. Chem. Ber. 1967, 100, 3172-3182.
9. Huisgen, R.; Dahmen, A.; Huber, H. J. Am. Chem. Soc. 1967, 89, 7130-7131.
10. Beaudry, C. M.; Malerich, J. P.; Trauner, D. Chem. Rev. 2005, 105, 4757-4778.
11. (a) Barbarow, J. E.; Miller, A. K.; Trauner, D. Org. Lett. 2005, 7, 2901-2903.
12. (b) Cueto, M.; D'Croz, L.; Mate, J. L.; San-Martin, A.; Darias, J. Org. Lett. 2005, 7, 415-418.
13. (c) Parker, K. A.; Wang, Z. Org. Lett. 2006, 8, 3553-3556.
14. Lawrence, A. L.; Wegner, H. A.; Jacobsen, M. F.; Adlington, R. M.; Baldwin, J. E. Tetrahedron Lett. 2006, 47, 8717-8720.
15. Vogt, P.; Schlageter, M.; Widmer, E. Tetrahedron Lett. 1991, 32, 4115-4116.
16. Pineschi, M.; Del Moro, F.; Crotti, P.; Macchia, F. Eur. J. Org. Chem. 2004, 2004, 4614-4620.
17. Snider, B. B.; Harvey, T. C. J. Org. Chem. 1994, 59, 504-506.
18. (a) Pohnert, G.; Boland, W. Tetrahedron 1994, 50, 10235-10244.
19. (b) Pohnert, G.; Boland, W. Nat. Prod. Reports 2002, 19, 108-122.
20. Hayashi, R.; Fernandez, S.; Okamura, W. H. Org. Lett. 2002, 4, 851-854.
21. (a) Kerr, D. J.; Willis, A. C.; Flynn, B. L. Org. Lett. 2004, 6, 457-460.
22. (b) Ma, S.; Gu, Z. J. Am. Chem. Soc. 2006, 128, 4942-4943.
23. (c) Zhu, Y.; Guo, Y.; Zhang, L.; Xie, D. J. Comput. Chem. 2007, 28, 2164-2169.
24. (a) Brückner, S.; Baldwin, J. E.; Adlington, R. M.; Claridge, T. D. W.; Odell, B. Tetrahedron 2004, 60, 2785-2788.
25. (b) Dell'Erba, C.; Mugnoli, A.; Novi, M.; Pertici, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 1999, 431-435.
26. (c) Magomedov, N. A.; Ruggiero, P. L.; Tang, Y. J. Am. Chem. Soc. 2004, 126, 1624-1625.
27. Salem, B.; Suffert, J. Angew. Chem., Int. Ed. 2004, 43, 2826-2830.
28. (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930.
29. (b) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757-5821.
30. (a) Bour, C.; Blond, G.; Salem, B.; Suffert, J. Tetrahedron 2006, 62, 10567-10581.
31. (b) Salem, B.; Klotz, P.; Suffert, J. Org. Lett. 2003, 5, 845-848.
32. (c) Salem, B.; Klotz, P.; Suffert, J. Synthesis 2004, 298-307.
33. (d) Suffert, J.; Salem, B.; Klotz, P. J. Am. Chem. Soc. 2001, 123, 12107-12108.
34. Lautens, M.; Smith, N. D.; Ostrovsky, D. J. Org. Chem. 1997, 62, 8970-8971.
35. Hulot, C.; Blond, G.; Suffert, J. J. Am. Chem. Soc. 2008, 130, 5046-5047.
36. (a) Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557.
37. (b) Rowley, M.; Kishi, Y. Tetrahedron Lett. 1988, 29, 4909-4912.
38. (c) Paquette, L. A.; Liang, S.; Galatsis, P. Synlett 1990, 663.
39. (d) Snider, B. M.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626.
40. (e) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Sobrino, A.; Vagberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909.
41. (f) Lo, P. C.-K.; Snapper, M. L. Org. Lett. 2001, 3, 2819-2821.
42. (g) Ruprah, P. K.; Cros, J.-P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 314, 5-3152. For excellent reviews in this field see:
43. (h) Keese, R. Chem. Rev. 2006, 106, 4787-4808.
44. (i) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720.
45. (j) Venepalli, B. R.; Agosta, W. C. Chem. Rev. 1987, 87, 399-410.
46. (k) Tellenbroker, J.; Kuck, D. Eur. J. Org. Chem. 2001, 1483-1489.
47. (l) Bredenkotter, B.; Barth, D.; Kuck, D. Chem. Commun. 1999, 847-848.
48. (m) Kuck, D. Liebigs Ann.-Recl. 1997, 1043-1057.
49. (n) Kuck, D.; Schuster, A.; Gestmann, D.; Posteher, F.; Pritzkow, H. Chem. Eur. J. 1996, 2, 58-67.
50. Gerber, P.; Keese, R. Tetrahedron Lett. 1992, 33, 3987.
51. (a) Wender, P. A. M.; Dore, T.; deLong, M. A. Tetrahedron Lett. 1996, 37, 7687.
52. (b) Wender, P. A.; deLong, M. A.; Wireko, F. C. Acta Crystallogr. 1997, C53, 954.
53. (c) Chappell, D.; Russell, A. T. Org. Biomol. Chem. 2006, 4409-4430.
54. (d) Cornelisse, J. Chem. Rev. 1993, 93, 615-669.
55. (e) McCullough, J. J. Chem. Rev. 1987, 87, 811-860.
56. (a) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473.
57. (b) De Keukeleire, D.; He, S. L. Chem. Rev. 1993, 93, 359-380.
58. (c) Crimmins, M. T.; Mascarella, S. W.; Bredon, L. D. Tetrahedron Lett. 1985, 26, 997-1000.
59. (d) Keese, R. Angew. Chem. Int. Ed. 1992, 31, 344-345.
60. (a) de Meijere, A. Chem. Rev. 2000, 100 (8), 2739-3282.
61. (b) Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789.
62. (c) Yet, L. Chem. Rev. 2000, 100, 2963.
63. (d) Tsuji, J. Transition Metal Reagents and Catalysts; Wiley & Sons: Sussex, 2000;
64. (e) Beller, M., Bolm, C., Eds. Transition Metals for Organic Synthesis; Wiley-VCH: Weinheim, 1998.
65. (f) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
66. (g) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
67. (h) Hartwig, J. F. In Comprehensive Coordination Chemistry II; Cleverty, Mc- J. A., Meyer, T. J., Eds.; Elsevier: Oxford, U.K., 2004; Vol.9, p 369.
68. (a) Kim, D. H.; Son, S. U.; Chung, Y. K.; Lee, S.-G. Chem. Commun. 2002, 56.
69. (b) Son, U. K.; Park, K. K. H.; Chung, Y. K. J. Am. Chem. Soc. 2002, 124, 6838.
70. Lindlar, H. Helv. Chim. Acta 1952, 35, 446-450.
71. (a) Aerssens, M. H. P. J.; Brandsma, L. J. Chem. Soc., Chem. Commun. 1984, 735-736.
72. (b) Aerssens, M. H.; Heiden, P. J.; van der, R.; Heus, M.; Brandsma, L. Synth. Commun. 1990, 20, 3421-3425.
73. (a) Brown, C. A. J. Org. Chem. 1970, 35, 1900-1904.
74. (b) Brown, C. A.; Ahuja, V. K. J. Org. Chem. 1973, 38, 2226-2230.
75. Choi, J.; Yoon, N. M. Tetrahedron Lett. 1996, 37, 1057-1060.
76. Brown, C. A.; Ahuja, V. K. J. Chem. Soc., Chem. Commun. 1973, 553-554.
77. Marshall, J. A.; Chobanian, H. R.; Yanik, M. M. Org. Lett. 2001, 3, 4107-4110.
78. Frisch, M. J., et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
79. (a) Schreiner, P. R. Angew. Chem., Int. Ed. 2007, 46, 4217-4219.
80. (b) Schreiner, P. R.; Fokin, A. A.; Pascal, R. A.; de Meijere, A. Org. Lett. 2006, 8, 3635-3638.
81. (c) Navarro-Vazquez, A.; Schreiner, P. R. J. Am. Chem. Soc. 2005, 127, 8150-8159.
82. Würthwein, E. U.; Chandrasekhar, J.; Jemmis, E. D.; Schleyer, P. v. R. Tetrahedron lett. 1981, 22, 843-846.
83. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
84. Heilbronner, E. Tetrahedron Lett. 1964, 29, 1923-1928.
85. Mauksch, M.; Gogonea, V.; Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. 1998, 37, 2395-2397.
86. Ajami, D.; Oeckler, O.; Simon, A.; Herges, R. Nature 2003, 426, 819-821.
87. Cope, A. C.; Haven, A. C.; Ramp, F. L.; Trumbull, E. R. J. Am. Chem. Soc. 1952, 74, 4867-4871.
88. (a) Freeman, F.; Hwang, J. H.; Junge, E. H.; Parmar, P. D.; Renz, Z.; Trinh, J. Int. J. Quantum Chem. 2008, 108, 339-350.
89. (b) Gill, G.; Pawar, D. M.; Noe, E. A J. Org. Chem. 2005, 70, 10726-10731.