Synthesis of dihydrobenzofurans with quaternary carbon center under mild and neutral conditions

Organic Letters

Volumn 15, Issue 17, 2013, Pages 4382-4385

  Takeda, Norihiko ^a   Ueda, Masafumi ^a   Kagehira, Syunsuke ^a   Komei, Hiroyuki ^a   Tohnai, Norimitsu ^b   Miyata, Mikiji ^b   Naito, Takeaki ^a   Miyata, Okiko ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; ETHER DERIVATIVE; NITRILE; OXIME;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

BENZOFURANS; CATALYSIS; CYCLIZATION; ETHERS; MOLECULAR STRUCTURE; NITRILES; OXIMES;

EID: 84883751651     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401897u     Document Type: Article

References (56)

1. Sheppard, T. D. J. Chem. Res. 2011, 35, 337
2. Ward, R. S. Nat. Prod. Rep. 1995, 183
3. Martin, S. F. In The Alkaloids; Brossi, A., Ed; Academic Press: New York, 1987; Vol. 30, pp 251-376.
4. Hoshino, O. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 51, pp 323-424.
5. Marco-Contelles, J.; Carreiras, M. D. C.; Rodriguez, C.; Villarroya, M.; Garcia, A. G. Chem. Rev. 2006, 106, 116
6. Santavy, F. In The Alkaloids; Manske, R. H. F.; Rodorico, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 385-519.
7. Taber, D. F.; Neubert, T. D.; Schlecht, M. F. The Enantioselective Synthesis of Morphine: Strategies and Tactics in Organic Synthesis 2004, 5, 353
8. Parker, K. A.; Fokas, D. J. Org. Chem. 2006, 71, 449
9. Poupat, C.; Husson, H.-P.; Rodriguez, B.; Husson, A.; Potier, P.; Janot, M.-M. Tetrahedron 1972, 28, 3087
10. Poupat, C.; Husson, H.-P.; Das, B. C.; Bladon, P.; Potier, P. Tetrahedron 1972, 28, 3103
11. Hamilton, C. J.; Saravanamuthu, A.; Poupat, C.; Fairlamb, A. H.; Eggleston, I. M. Bioorg. Med. Chem. 2005, 14, 2266
12. Chen, P.; Bao, X.; Zhang, L.-F.; Ding, M.; Han, X.-J.; Li, J.; Zhang, G.-B.; Tu, Y.-Q.; Fan, C.-A. Angew. Chem., Int. Ed. 2011, 50, 8161
13. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303
14. Fernandez, R.; Martin, M. J.; Rodriguez-Acebes, R.; Reyes, F.; Francesch, A.; Cuevas, C. Tetrahedron Lett. 2008, 49, 2282
15. Nicolaou, K. C.; Chen, D. Y.-K.; Huang, X.; Ling, T.; Bella, M.; Snyder, S. A. J. Am. Chem. Soc. 2004, 126, 12888
16. Knowles, R. R.; Carpenter, J.; Blakey, S. B.; Kayano, A.; Mangion, I. K.; Sinz, C. J.; MacMillan, D. W. C. Chem. Sci 2011, 2, 308
17. Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takeda, T. J. Org. Chem. 1998, 63, 6625
18. Kodama, S.; Hamashima, Y.; Nishida, K.; Node, M. Angew. Chem., Int. Ed. 2004, 43, 2659
19. Node, M.; Kodama, S.; Hamashima, Y.; Kato, T.; Nishida, K.; Kajimoto, T. Chem. Pharm. Bull. 2006, 54, 1662
20. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 11262
21. Trost, B. M.; Tang, W. Angew. Chem., Int. Ed. 2002, 41, 2759
22. Troste, B. M.; Tang, W.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 14785
23. Hsin, L.-W.; Chang, L.-T.; Chen, C.-W.; Hsu, C.-H.; Chen, H.-W. Tetrahedron 2005, 61, 513
24. Chen, J.-Q.; Xie, J.-H.; Bao, D.-H.; Liu, S.; Zhou, Q.-L. Org. Lett. 2012, 14, 2714
25. Tanimoto, H.; Kato, T.; Chida, N. Tetrahedron Lett. 2007, 48, 6267
26. Kato, T.; Tanimoto, H.; Yamada, H.; Chida, N. Heterocycles 2010, 82, 563
27. Malachowski, W. P.; Paul, T.; Phounsavath, S. J. Org. Chem. 2007, 72, 6792
28. Magnus, P.; Sane, N.; Fauber, B. P.; Lynch, V. J. Am. Chem. Soc. 2009, 131, 16045
29. Fan, C.-A.; Tu, Y.-Q.; Song, Z.-L.; Zhang, E.; Shi, L.; Wang, M.; Wang, B.; Zhang, S.-Y. Org. Lett. 2004, 6, 4691
30. Sheradsky, T. Tetrahedron Lett. 1966, 5225
31. Maimone, T. J.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 9990
32. Contiero, F.; Jones, K. M.; Matts, E. A.; Porzello, A.; Tomkinson, N. C. O. Synlett 2009, 3003
33. Benzofuran synthesis by the Au-catalyzed tandem condensation/ rearrangement/cyclization reaction of O -arylhydroxylamine with 1,3-dicarbonyl compounds has been reported: Liu, Y.; Qian, J.; Lou, S.; Xu, Z. J. Org. Chem. 2010, 75, 6300
34. Kaminsky, D.; Shavel, J., Jr.; Meltzer, R. I. Tetrahedron Lett. 1967, 8, 859
35. Symmetrically α,α′-disubstituted oxime ether is known to give the dihydrobenzofuran with quarternary carbon under acidic and thermal conditions; see: Laronze, J.-Y.; Boukili, R. E.; Patigny, D.; Dridi, S.; Cartier, D.; Lévy, J. Tetrahedron 1991, 47, 10003
36. Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299
37. Bernardi, L.; Fochi, M.; Franchini, M. C.; Ricci, A. Org. Biomol. Chem. 2012, 10, 2911
38. Pirrung, M. C. Chem.-Eur. J. 2006, 12, 1312
39. Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289
40. Lindström, U. F. Chem. Rev. 2002, 102, 2751
41. Severance, D. L.; Jorgensen, W. L. J. Am. Chem. Soc. 1992, 114, 10966
42. Jorgensen, W. L.; Blake, J. F.; Lim, D.; Severance, D. L. J. Chem. Soc., Faraday Trans. 1994, 90, 1727
43. Davidson, M. M.; Hillier, I. H. J. Phys. Chem. 1995, 99, 6748
44. Ganem, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 936
45. Mark, M. D.; Ian, H. H. J. Phys. Chem. 1995, 99, 6748
46. Gajewski, J. J. J. Org. Chem. 1992, 57, 5500
47. Gajewski, J. J. Acc. Chem. Res. 1997, 30, 219
48. "Structure and Reactivity in Aqueous Solution": Gajewski, J. J.; Brichford, N. L. ACS Symp. Ser. 1994, 568, 229
49. Severance, D. L.; Jorgensen, W. L. J. Am. Chem. Soc. 1992, 114, 10966
50. Curran, D. P.; Kuo, L. H. Tetrahedron Lett. 1995, 36, 6647
51. Kirsten, M.; Rehbein, J.; Hiersemann, M.; Strassner, T. J. Org. Chem. 2007, 72, 4001
52. Uyeda, C.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 9228
53. Annamalai, V. R.; Linton, E. C.; Kozlowski, M. C. Org. Lett. 2009, 11, 621
54. Takeda, N.; Miyata, O.; Naito, T. Eur. J. Org. Chem. 2007, 1491
55. Takeda, N.; Miyata, O.; Kitamura, M.; Kagehira, S.; Naito, T. Synlett 2006, 3415
56. Miyata, O.; Takeda, N.; Naito, T. Heterocycles 2009, 78, 843