Using nazarov electrocyclization to stage chemoselective [1,2]-migrations: Stereoselective synthesis of functionalized cyclopentenones

Angewandte Chemie - International Edition

Volumn 50, Issue 46, 2011, Pages 10981-10985

  Lebœuf, David ^a   Huang, Jie ^a   Gandon, Vincent ^b   Frontier, Alison J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

copper; density functional calculations; homogeneous catalysis; Nazarov cyclization; Wagner Meerwein rearrangement

Indexed keywords

CHEMOSELECTIVE; COPPER (II); CYCLOPENTENONES; DENSITY-FUNCTIONAL CALCULATIONS; DFT STUDY; ELECTROCYCLIZATION; FUNCTIONALIZED; HOMOGENEOUS CATALYSIS; NAZAROV CYCLIZATION; STEREOSELECTIVE SYNTHESIS; STERIC BULK; WAGNER-MEERWEIN REARRANGEMENT;

REACTION KINETICS; STEREOCHEMISTRY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

CYCLIZATION;

COPPER; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; ELECTRON; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COPPER; CYCLIZATION; CYCLOPENTANES; ELECTRONS; STEREOISOMERISM;

EID: 80855156732     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201104870     Document Type: Article

References (80)

1. C. Santelli-Rouvier, M. Santelli, Synthesis 1983, 429
2. K. L. Habermas, S. E. Denmark, T. K. Jones, in Organic Reactions, Vol. 45 (Ed.:, L. A. Paquette,), Wiley, New York, 1994, pp. 1-158
3. M. Harmata, Chemtracts 2004, 17, 416
4. H. Pellissier, Tetrahedron 2005, 61, 6479
5. A. J. Frontier, C. Collison, Tetrahedron 2005, 61, 7577
6. M. A. Tius, Eur. J. Org. Chem. 2005, 2193
7. N. Shimada, C. Stewart, M. A. Tius, Tetrahedron 2011, DOI:.
8. D. R. Williams, L. A. Robinson, C. R. Nevill, J. P. Reddy, Angew. Chem. 2007, 119, 933
9. Angew. Chem. Int. Ed. 2007, 46, 915
10. W. He, J. Huang, X. Sun, A. J. Frontier, J. Am. Chem. Soc. 2008, 130, 300
11. A. P. Marcus, A. S. Lee, R. L. Davis, D. J. Tantillo, R. Sarpong, Angew. Chem. 2008, 120, 6479
12. Angew. Chem. Int. Ed. 2008, 47, 6379
13. C. J. Rieder, K. J. Winberg, F. G. West, J. Am. Chem. Soc. 2009, 131, 7504
14. J. A. Malona, K. Cariou, A. J. Frontier, J. Am. Chem. Soc. 2009, 131, 7560
15. R. Singh, M. K. Parai, G. Panda, Org. Biomol. Chem. 2009, 7, 1858
16. P. Cordier, C. Aubert, M. Malacria, E. Lacôte, V. Gandon, Angew. Chem. 2009, 121, 8913
17. Angew. Chem. Int. Ed. 2009, 48, 8757
18. M. Wang, F. Han, H. Yuan, Q. Liu, Chem. Commun. 2010, 46, 2247
19. P. A. Wender, R. T. Stemmler, L. E. Sirois, J. Am. Chem. Soc. 2010, 132, 2532
20. K. Murugan, S. Srimurugan, C. Chen, Chem. Commun. 2010, 46, 1127
21. D. J. Kerr, J. M. White, B. L. Flynn, J. Org. Chem. 2010, 75, 7073
22. A. P. Marcus, R. Sarpong, Org. Lett. 2010, 12, 4560
23. Z. Cai, M. Harmata, Org. Lett. 2010, 12, 5668.
24. V. K. Aggarwal, A. J. Belfield, Org. Lett. 2003, 5, 5075
25. G. Liang, D. Trauner, J. Am. Chem. Soc. 2004, 126, 9544
26. M. Rueping, W. Ieawsuwan, A. P. Antonchick, B. J. Nachtscheim, Angew. Chem. 2007, 119, 2143
27. Angew. Chem. Int. Ed. 2007, 46, 2097
28. A. R. Banaag, M. A. Tius, J. Org. Chem. 2008, 73, 8133
29. I. Walz, A. Togni, Chem. Commun. 2008, 4315
30. M. Rueping, W. Ieawsuwan, Adv. Synth. Catal. 2009, 351, 78
31. K. Yaji, M. Shindo, Synlett 2009, 2524
32. P. Cao, C. Deng, Y.-Y. Zhou, X.-L. Sun, J.-C. Zheng, W. Xie, Y. Tang, Angew. Chem. 2010, 122, 4565
33. Angew. Chem. Int. Ed. 2010, 49, 4463
34. W. F. Bow, A. K. Basak, A. Jolit, D. A. Vicic, M. A. Tius, Org. Lett. 2010, 12, 440
35. A. K. Basak, N. Shimada, W. F. Bow, D. A. Vicic, M. A. Tius, J. Am. Chem. Soc. 2010, 132, 8266.
36. W. He, X. Sun, A. J. Frontier, J. Am. Chem. Soc. 2003, 125, 14278
37. II
38. C. Bee, E. Leclerc, M. A. Tius, Org. Lett. 2003, 5, 4927
39. III
40. P. Larini, A. Guarna, E. G. Occhiato, Org. Lett. 2006, 8, 781
41. J. A. Malona, J. M. Colbourne, A. J. Frontier, Org. Lett. 2006, 8, 5661
42. III
43. M. Janka, W. He, A. J. Frontier, R. Eisenberg, J. Am. Chem. Soc. 2004, 126, 6864
44. M. Janka, W. He, A. J. Frontier, C. Flaschenriem, R. Eisenberg, Tetrahedron 2005, 61, 6193
45. T. Vaidya, A. C. Atesin, I. R. Herrick, A. J. Frontier, R. Eisenberg, Angew. Chem. 2010, 122, 3435
46. Angew. Chem. Int. Ed. 2010, 49, 3363
47. IV
48. I
49. L. Zhang, S. Wang, J. Am. Chem. Soc. 2006, 128, 1442
50. T. Jin, Y. Yamamoto, Org. Lett. 2008, 10, 3137
51. I
52. M. Kawatsura, K. Kajita, S. Hayase, T. Itoh, Synlett 2010, 1243.
53. T. N. Grant, C. J. Rieder, F. G. West, Chem. Commun. 2009, 5676, and references therein. For other relevant examples, see
54. F. Dhoro, T. E. Kristensen, V. Stockmann, G. P. A. Yap, M. A. Tius, J. Am. Chem. Soc. 2007, 129, 7256
55. V. M. Marx, D. J. Burnell, Org. Lett. 2009, 11, 1229
56. V. M. Marx, D. J. Burnell, J. Am. Chem. Soc. 2010, 132, 1685
57. C. J. Rieder, R. J. Fradette, F. G. West, Heterocycles 2010, 80, 1413
58. O. Scadeng, F. G. West, Org. Lett. 2011, 13, 114
59. V. M. Marx, F. M. LeFort, D. J. Burnell, Adv. Synth. Catal. 2011, 353, 64.
60. G. Ohloff, K. H. Schulte-Elte, E. Demole, Helv. Chim. Acta 1971, 54, 2913
61. L. A. Paquette, W. E. Fristad, D. S. Dime, T. R. Bailey, J. Org. Chem. 1980, 45, 3017
62. S. E. Denmark, G. A. G. Hite, Helv. Chim. Acta 1988, 71, 195
63. J. Motoyoshiya, T. Yazaki, S. Hayashi, J. Org. Chem. 1991, 56, 735
64. A. G. Gruhn, W. Reusch, Tetrahedron 1993, 49, 8159
65. C. Kuroda, H. Koshio, A. Koito, H. Sumiya, A. Murase, Y. Hirono, Tetrahedron 2000, 56, 6441
66. P. Chiu, S. L. Li, Org. Lett. 2004, 6, 613.
67. J. Huang, A. J. Frontier, J. Am. Chem. Soc. 2007, 129, 8060
68. J. Huang, D. Lebœuf, A. J. Frontier, J. Am. Chem. Soc. 2011, 133, 6307.
69. M. A. Brimble, D. Crimmins, M. Trzoss, Arkivoc 2005, i, 39.
70. W. F. Bachmann, J. W. Ferguson, J. Am. Chem. Soc. 1934, 56, 2081
71. C. J. Collins, J. Am. Chem. Soc. 1955, 77, 5517
72. J. R. Owen, W. H. Saunders, J. Am. Chem. Soc. 1966, 88, 5809
73. R. L. Heidke, W. H. Saunders, J. Am. Chem. Soc. 1966, 88, 5816.
74. G. W. T. M. J. Frisch, et al. Gaussian 03 (v C02), Gaussian, Inc., Wallingford CT, 2004. See the Supporting Information of the full citation.
75. J. A. Mayoral, S. Rodríguez-Rodríguez, L. Salvatella, Chem. Eur. J. 2008, 14, 9274; for selected theoretical reports on proton-mediated Nazarov reactions, see
76. O. Nieto Faza, C. Silva López, R. Úlvarez, A. R. de Lera, Chem. Eur. J. 2004, 10, 4324
77. A. Cavalli, M. Masetti, M. Recanatini, C. Prandi, A. Guarna, E. G. Occhiato, Chem. Eur. J. 2006, 12, 2836
78. A. Cavalli, A. Pacetti, M. Recanatini, C. Prandi, D. Scarpi, E. G. Occhiato, Chem. Eur. J. 2008, 14, 9292
79. R. L. Davis, D. J. Tantillo, Curr. Org. Chem. 2010, 14, 1561; for a theoretical report on the retro-Nazarov reaction, see
80. M. Harmata, P. R. Schreiner, D. R. Lee, P. L. Kirchhoefer, J. Am. Chem. Soc. 2004, 126, 10954.