Asymmetric Brønsted acid-catalyzed Nazarov cyclization of acyclic α-alkoxy dienones

Chemistry - An Asian Journal

Volumn 7, Issue 10, 2012, Pages 2361-2366

  Raja, Sadiya ^a   Ieawsuwan, Winai ^a   Korotkov, Vadim ^a   Rueping, Magnus ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

asymmetric synthesis; Br nsted acids; electrocyclizations; Nazarov reaction; organocatalysis

Indexed keywords

ASYMMETRIC SYNTHESIS; CYCLOPENTENONES; DIENONES; ELECTROCYCLIZATION REACTIONS; ELECTROCYCLIZATIONS; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; NAZAROV CYCLIZATION; NAZAROV REACTION; OPTICALLY ACTIVE; ORGANOCATALYSIS;

ENANTIOSELECTIVITY; REACTION KINETICS;

CYCLIZATION;

ACID; ALCOHOL DERIVATIVE; ALKOXY RADICAL; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

ACIDS; ALCOHOLS; CATALYSIS; CYCLIZATION; CYCLOPENTANES; STEREOISOMERISM;

EID: 84866352330     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201200391     Document Type: Article

References (63)

1. M. Mikolajczyk, M. Mikina, R. Zurawinski, Pure Appl. Chem. 1999, 71, 473-480
2. S. Das, S. Chandrasekhar, J. S. Jadav, R. Grée, Chem. Rev. 2007, 107, 3286-3337.
3. S. E. Gibson, S. E. Lewis, N. Mainolfi, J. Organomet. Chem. 2004, 689, 3873-3890.
4. K. L. Habermas, S. E. Denmark, T. K. Jones, Org. React. 1994, 45, 1-158
5. S. E. Denmark, in Comprehensive Organic Synthesis, Vol. 5 (Eds.:, B. M. Trost, I. Flemming,), Pergamon, Oxford, 1991, p. 751-784
6. A. J. Frontier, C. Collison, Tetrahedron 2005, 61, 7577-7606
7. H. Pellissier, Tetrahedron 2005, 61, 6479-6517
8. M. A. Tius, Eur. J. Org. Chem. 2005, 2193-2206
9. W. Nakanishi, F. G. West, Curr. Opin. Drug Discovery Dev. 2009, 12, 732-751
10. N. Shimada, C. Stewart, M. A. Tius, Tetrahedron 2011, 67, 5851-5870
11. T. Vaidya, R. Eisenberg, A. J. Frontier, ChemCatChem 2011, 3, 1531-1548.
12. G. Liang, S. N. Gradl, D. Trauner, Org. Lett. 2003, 5, 4931-4934
13. V. K. Aggarwal, A. J. Belfield, Org. Lett. 2003, 5, 5075-5078
14. G. Liang, D. Trauner, J. Am. Chem. Soc. 2004, 126, 9544-9545
15. I. Walz, A. Togni, Chem. Commun. 2008, 4315-4317
16. K. Yaji, M. Shindo, Synlett 2009, 14, 2524-2528
17. P. Cao, C. Deng, Y.-Y. Zhou, X.-L. Sun, J.-C. Zheng, Z. Xie, Y. Tang, Angew. Chem. 2010, 122, 4565-4568
18. Angew. Chem. Int. Ed. 2010, 49, 4463-4466
19. M. Kawatsura, K. Kajita, S. Hayase, T. Itoh, Synlett 2010, 8, 1243-1246
20. J. Huang, D. Leboeuf, A. J. Frontier, J. Am. Chem. Soc. 2011, 133, 6307-6317; for enantioselective tandem Nazarov- fluorination reaction, see
21. J. Nie, H.-W. Zhu, H.-F. Cui, M.-Q. Hua, J.-A. Ma, Org. Lett. 2007, 9, 3053-3056
22. H.-F. Cui, K.-Y. Dong, G.-W. Zhang, L. Wang, J.-A. Ma, Chem. Commun. 2007, 2284-2286; for tandem Nazarov cyclization Michael addition, see
23. M. Janka, W. He, I. E. Haedicke, F. R. Fronczek, A. J. Frontier, R. Eisenberg, J. Am. Chem. Soc. 2006, 128, 5312-5313.
24. A. K. Basak, N. Shimada, W. F. Bow, D. A. Vicic, M. A. Tius, J. Am. Chem. Soc. 2010, 132, 8266-8267; Nazarov cyclization with stoechiometric amounts of chiral diamines
25. W. F. Bow, A. K. Basak, A. Jolit, D. A. Vicic, M. A. Tius, Org. Lett. 2010, 12, 440-443
26. Asymmetric aza-Nazarov cyclization:, N. Shimada, B. O. Ashburn, A. K. Basak, W. F. Bow, D. A. Vicic, M. A. Tius, Chem. Commun. 2010, 46, 3774-3775.
27. M. Rueping, W. Ieawsuwan, A. P. Antonchick, B. J. Nachtsheim, Angew. Chem. 2007, 119, 2143-2146
28. Angew. Chem. Int. Ed. 2007, 46, 2097-2100.
29. T. Akiyama, Chem. Rev. 2007, 107, 5744-5758
30. T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010
31. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573
32. Angew. Chem. Int. Ed. 2006, 45, 1520-1543
33. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743
34. H. Yamamoto, N. Payette, in Hydrogen Bonding in Organic Synthesis (Ed.:, P. M. Pihko,), Wiley-VCH, Weinheim, 2009, pp. 73-140
35. D. Kampen, C. M. Reisinger, B. List, Top. Curr. Chem. 2009, 291, 395-456
36. M. Terada, Synthesis 2010, 1929-1982
37. M. Rueping, A. Kuenkel, I. Atodiresei, Chem. Soc. Rev. 2011, 40, 4539-4549.
38. M. Rueping, W. Ieawsuwan, Adv. Synth. Catal. 2009, 351, 78-84
39. M. Rueping, W. Ieawsuwan, Chem. Commun. 2011, 47, 11450-11452.
40. S. A. Yamamoto, D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626-9627
41. P. Jiao, D. Nakashima, H. Yamamoto, Angew. Chem. 2008, 120, 2445-2447
42. Angew. Chem. Int. Ed. 2008, 47, 2411-2413
43. C. H. Cheon, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 9246-9247
44. M. Rueping, B. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603-606
45. Angew. Chem. Int. Ed. 2008, 47, 593-596
46. M. Rueping, T. Theissmann, A. Kuenkel, R. M. Koenigs, Angew. Chem. 2008, 120, 6903-6906
47. Angew. Chem. Int. Ed. 2008, 47, 6798-6801
48. M. Rueping, A. P. Antonchick, Angew. Chem. 2008, 120, 10244-10247
49. Angew. Chem. Int. Ed. 2008, 47, 10090-10093
50. D. Enders, A. A. Narine, F. Toulgoat, T. Bisschops, Angew. Chem. 2008, 120, 5744-5748
51. Angew. Chem. Int. Ed. 2008, 47, 5661-5665
52. M. Zeng, Q. Kang, Q.-L. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 2169-2173
53. M. Rueping, M.-Y. Lin, Chem. Eur. J. 2010, 16, 4169-4172
54. M. Rueping, B. J. Nachtsheim, Synlett 2010, 119-122
55. M. Rueping, E. Merino, R. M. Koenigs, Adv. Synth. Catal. 2010, 352, 2629-2634
56. C. H. Cheon, H. Yamamoto, Org. Lett. 2010, 12, 2476-2479
57. Z. Feng, Q.-L. Xu, L.-X. Dai, S.-L. You, Heterocycles 2010, 80, 765-771
58. M. Rueping, U. Uria, M.-Y. Lin, I. Atodiresei, J. Am. Chem. Soc. 2011, 133, 3732-3735
59. T. Hashimoto, H. Nakatsu, K. Yamamoto, K. Maruoka, J. Am. Chem. Soc. 2011, 133, 9730-9733.
60. M. Rueping, B. J. Nachtsheim, R. M. Koenigs, W. Ieawsuwan, Chem. Eur. J. 2010, 16, 13116-13126
61. M. Rueping, B. J. Nachtsheim, W. Ieawsuwan, I. Atodiresei, Angew. Chem. 2011, 123, 6838-6853
62. Angew. Chem. Int. Ed. 2011, 50, 6706-6720.
63. During the preparation of this manuscript an elegant application of this method for synthesis of roseophilin was reported, see:, D. J. Kerr, B. L. Flynn, Org. Lett. 2012, 14, 1740-1743.