Asymmetric Nazarov cyclizations

Tetrahedron

Volumn 67, Issue 33, 2011, Pages 5851-5870

  Shimada, Naoyuki ^a   Stewart, Craig ^a   Tius, Marcus A ^a,b  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF HAWAII CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; NAZAROV CYCLIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 79960224466     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.062     Document Type: Review

References (67)

1. I.N. Nazarov, and I.I. Zaretskaya Izv. Akad. Nauk SSSR, Ser. Khim. 1941 211 224
2. I.N. Nazarov, and I.I. Zaretskaya Zh. Obshch. Khim. 27 1957 693 713
3. I.N. Nazarov, I.I. Zaretskaya, and T.I. Sorkina Zh. Obshch. Khim. 30 1960 746 754
4. W. Nakanishi, and F.G. West Curr. Opin. Drug Discovery Dev. 12 2009 732 751
5. T.N. Grant, C.J. Rieder, and F.G. West Chem. Commun. 2009 5676 5688
6. A.J. Frontier, and C. Collison Tetrahedron 61 2005 7577 7606
7. H. Pellissier Tetrahedron 61 2005 6479 6517
8. M.A. Tius Eur. J. Org. Chem. 2005 2193 2206
9. M. Harmata Chemtracts 17 2004 416 435
10. M.A. Tius Acc. Chem. Res. 36 2003 284 290
11. K.L. Habermas, S. Denmark, and T.K. Jones L.A. Paquette, Organic Reactions Vol. 45 1994 John Wiley New York, NY 1 158
12. K. Krohn Org. Synth. Highlights 1991 137 144
13. C. Santelli-Rouvier, and M. Santelli Synthesis 1983 429 442
14. R.B. Bates, and D.A. McCombs Tetrahedron Lett. 10 1969 977 978
15. C.W. Shoppee, and G.N. Henderson J. Chem. Soc., Chem. Commun. 1974 561 562
16. D.R. Williams, J.T. Reeves, P.P. Nag, W.H. Pitcock Jr., and M.-H. Baik J. Am. Chem. Soc. 128 2006 12339 12348
17. M. Rueping, W. Ieawsuwan, A.P. Antonchick, and B.J. Nachtsheim Angew. Chem., Int. Ed. 46 2007 2097 2100
18. S. Casson, and P. Kocienski J. Chem. Soc., Perkin Trans. 1 1994 1187 1191
19. W. He, X. Sun, and A.J. Frontier J. Am. Chem. Soc. 125 2003 14278 14279
20. M.A. Tius, C.-K. Kwok, X.-Q. Gu, and C. Zhao Synth. Commun. 24 1994 871 885
21. M. Rueping, and W. Ieawsuwan Adv. Synth. Catal. 351 2009 78 84
22. G. Pousse, A. Devineau, V. Dalla, L. Humphreys, M.-C. Lasne, J. Rouden, and J. Blanchet Tetrahedron 65 2009 10617 10622
23. A.K. Basak, N. Shimada, W.F. Bow, D.A. Vicic, and M.A. Tius J. Am. Chem. Soc. 132 2010 8266 8267
24. G. Liang, and D. Trauner J. Am. Chem. Soc. 126 2004 9544 9545
25. G. Liang, S.N. Gradl, and D. Trauner Org. Lett. 5 2003 4931 4934
26. J. Nie, H.-W. Zhu, H.-F. Cui, M.-Q. Hua, and J.-A. Ma Org. Lett. 9 2007 3053 3056
27. K. Yaji, and M. Shindo Synlett 2009 2524 2528
28. M. Kawatsura, K. Kajita, S. Hayase, and T. Itoh Synlett 2010 1243 1246
29. P. Cao, C. Deng, Y.-Y. Zhou, X.-L. Sun, J.-C. Zheng, Z. Xie, and Y. Tang Angew. Chem., Int. Ed. 49 2010 4463 4466
30. J. Huang, and A.J. Frontier J. Am. Chem. Soc. 129 2007 8060 8061
31. M. Kokubo, and S. Kobayashi Chem. - Asian J. 4 2009 526 528
32. I. Walz, and A. Togni Chem. Commun. 2008 4315 4317
33. V.K. Aggarwal, and A.J. Belfield Org. Lett. 5 2003 5075 5078
34. W.F. Bow, A.K. Basak, A. Jolit, D.A. Vicic, and M.A. Tius Org. Lett. 12 2010 440 443
35. See also: N. Shimada, B.O. Ashburn, A.K. Basak, W.F. Bow, D.A. Vicic, and M.A. Tius Chem. Commun. 2010 3774 3775
36. S.E. Denmark, M.A. Wallace, and C.B. Walker Jr. J. Org. Chem. 55 1990 5543 5545
37. H. Hu, D. Smith, R.E. Cramer, and M.A. Tius J. Am. Chem. Soc. 121 1999 9895 9896
38. C. Schultz-Fademrecht, M.A. Tius, S. Grimme, B. Wibbeling, and D. Hoppe Angew. Chem., Int. Ed. 41 2002 1532 1535
39. M. Zimmermann, B. Wibbeling, and D. Hoppe Synthesis 2004 765 774
40. D.R. Williams, L.A. Robinson, C.R. Nevill, and J.P. Reddy Angew. Chem., Int. Ed. 46 2007 915 918
41. J. Forest, C. Bee, F. Cordaro, and M.A. Tius Org. Lett. 5 2003 4069 4072
42. W.A. Batson, D. Sethumadhavan, and M.A. Tius Org. Lett. 7 2005 2771 2774
43. S. Gao, Q. Wang, and C. Chen J. Am. Chem. Soc. 131 2009 1410 1412
44. S. Gao, Q. Wang, L.J.-S. Huang, L. Lum, and C. Chen J. Am. Chem. Soc. 132 2010 371 383
45. F. Churruca, M. Fousteris, Y. Ishikawa, M.W. Rekowski, C. Hounsou, T. Surrey, and A. Giannis Org. Lett. 12 2010 2096 2099
46. R. Noyori, Y. Ohnishi, and M. Kato Tetrahedron Lett. 19 1971 1515 1518
47. J.K. Crandall, and R.P. Haseltine J. Am. Chem. Soc. 90 1968 6251 6253
48. J. Leitich, I. Heise, S. Werner, C. Krueger, and K. Schaffner J. Photochem. Photobiol. A: Chem. 57 1991 127 151
49. See also: A.R. Matlin, and K. Jin Tetrahedron Lett. 30 1989 637 640
50. J. Leitich, I. Heise, J. Rust, and K. Schaffner Eur. J. Org. Chem. 2001 2719 2726
51. See also: A.B. Smith III, and W.C. Agosta J. Am. Chem. Soc. 95 1973 1961 1968
52. R.D. Mazzola Jr., T.D. White, H.R. Vollmer-Snarr, and F.G. West Org. Lett. 7 2005 2799 2801
53. For related studies see: C. Liu, and J.R. Sowa Jr. Tetrahedron Lett. 37 1996 7241 7244
54. Y.-K. Wu, and F.G. West J. Org. Chem. 75 2010 5410 5413
55. C. Prandi, A. Ferrali, A. Guarna, P. Venturello, and E.G. Occhiato J. Org. Chem. 69 2004 7705 7709
56. For related studies see: A. Srikrishna, and G. Neetu Tetrahedron: Asymmetry 21 2010 2067 2071
57. E.G. Occhiato, C. Prandi, A. Ferrali, and A. Guarna J. Org. Chem. 70 2005 4542 4545
58. L.N. Pridgen, K. Huang, S. Shilcrat, A. Tickner-Eldridge, C. DeBrosse, and R.C. Haltiwanger Synlett 1999 1612 1614
59. D.J. Kerr, C. Metje, and B.L. Flynn Chem. Commun. 2003 1380 1381
60. D.J. Kerr, J.M. White, and B.L. Flynn J. Org. Chem. 75 2010 7073 7084
61. P.E. Harrington, and M.A. Tius Org. Lett. 2 2000 2447 2450
62. D.B. delos Santos, A.R. Banaag, and M.A. Tius Org. Lett. 8 2006 2579 2582
63. A.R. Banaag, and M.A. Tius J. Am. Chem. Soc. 129 2007 5328 5329
64. A.R. Banaag, and M.A. Tius J. Org. Chem. 73 2008 8133 8141
65. P.E. Harrington, and M.A. Tius J. Am. Chem. Soc. 123 2001 8509 8514
66. P.E. Harrington, T. Murai, C. Chu, and M.A. Tius J. Am. Chem. Soc. 124 2002 10091 10100
67. F. Dhoro, T.E. Kristensen, V. Stockmann, G.P.A. Yap, and M.A. Tius J. Am. Chem. Soc. 129 2007 7256 7257