Grignard reagent acceleration of the intramolecular diels-alder reaction of furans with unactivated alkynes: Towards structurally complex oxabicyclic alkenes

Chemistry - A European Journal

Volumn 17, Issue 45, 2011, Pages 12582-12586

  Chen, Yifeng ^a   Wang, Lu ^a   Liu, Yuanhong ^a   Li, Yuxue ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

alkynes; Diels Alder reaction; domino reactions; furans; Grignard reaction; stereoselectivity

Indexed keywords

ALKYNES; DIELS-ALDER REACTION; DOMINO REACTIONS; FURANS; GRIGNARD REACTION;

ACETYLENE; CHELATION; KETONES; MAGNESIUM; OLEFINS; ORGANIC POLLUTANTS; REACTION RATES; STEREOSELECTIVITY;

AROMATIC COMPOUNDS;

EID: 80054947887     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102028     Document Type: Article

References (59)

1. W. R. Roush, in Comprehensive Organic Synthesis, Vol. 5 (Eds.:, B. M. Trost, I. Flemming, L. A. Paquette,), Pergamon, Oxford, 1991, Chapter 4.1, pp. 513-550
2. F. Fringuelli, A. Taticchi, The Diels-Alder Reaction: Selected Practical Methods, Wiley, New York, 2002
3. K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742
4. Angew. Chem. Int. Ed. 2002, 41, 1668.
5. B. H. Lipshutz, Chem. Rev. 1986, 86, 795
6. C. O. Kappe, S. S. Murphree, A. Padwa, Tetrahedron 1997, 53, 14179.
7. A. Padwa, H. Zhang, J. Org. Chem. 2007, 72, 2570
8. A. Padwa, Q. Wang, J. Org. Chem. 2006, 71, 7391
9. Q. Wang, A. Padwa, Org. Lett. 2004, 6, 2189
10. J. D. Ginn, A. Padwa, Org. Lett. 2002, 4, 1515
11. S. Claeys, V. D. Haver, P. J. De Clercq, M. Milanesio, D. Viterbo, Eur. J. Org. Chem. 2002, 1051
12. S. E. Wolkenberg, D. L. Boger, J. Org. Chem. 2002, 67, 7361
13. A. Padwa, M. A. Brodney, S. M. Lynch, J. Org. Chem. 2001, 66, 1716
14. C. C. Li, S. Liang, X. Zhang, Z. Xie, J. Chen, Y. Wu, Z. Yang, Org. Lett. 2005, 7, 3709.
15. D. K. Rayabarapu, C. H. Cheng, Acc. Chem. Res. 2007, 40, 971
16. M. Lautens, K. Fagnou, S. Hiebert, Acc. Chem. Res. 2003, 36, 48.
17. A. S. K. Hashmi, M. Rudolph, J. Huck, W. Frey, J. W. Bats, M. HamziÄ, Angew. Chem. 2009, 121, 5962
18. Angew. Chem. Int. Ed. 2009, 48, 5848
19. Y. Chen, Y. Lu, G. Li, Y. Liu, Org. Lett. 2009, 11, 3838
20. Y. Chen, G. Li, Y. Liu, Adv. Synth. Catal. 2011, 353, 392; for selected papers involving terminal alkynes
21. A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553
22. A. S. K. Hashmi, L. Ding, P. Fischer, J. W. Bats, W. Frey, Chem. Eur. J. 2003, 9, 4339; for Pt-catalyzed reactions, see
23. B. Martín-Matute, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2003, 125, 5757.
24. For an intramolecular Diels-Alder reaction of furan with a propargyl amide bearing an internal alkyne moiety through an intermediate isomeric allenamide, see:, A. G. Lohse, R. P. Hsung, Org. Lett. 2009, 11, 3430.
25. H. J. Wu, F. H. Ying, W. D. Shao, J. Org. Chem. 1995, 60, 6168
26. H. J. Wu, W. D. Shao, F. H. Ying, Tetrahedron Lett. 1994, 35, 729
27. K. Kanematsu, I. Kinoyama, J. Chem. Soc., Chem. Commun. 1992, 735.
28. T. Mukaiyama, T. Tsuji, N. Iwasawa, Chem. Lett. 1979, 697
29. T. Mukaiyama, T. Takebayashi, Chem. Lett. 1980, 1013
30. T. Takebayashi, N. Iwasawa, T. Mukaiyama, Bull. Chem. Soc. Jpn. 1983, 56, 1107.
31. G. Stork, T. Y. Chan, G. A. Breault, J. Am. Chem. Soc. 1992, 114, 7578
32. S. M. Sieburth, L. Fensterbank, J. Org. Chem. 1992, 57, 5279; for Mg, see
33. G. Stork, T. Y. Chan, J. Am. Chem. Soc. 1995, 117, 6595
34. D. E. Ward, M. S. Abaee, Org. Lett. 2000, 2, 3937; For B
35. R. A. Batey, A. N. Thadani, A. J. Lough, J. Am. Chem. Soc. 1999, 121, 450; for Zn and Al, see
36. F. Bertozzi, R. Olsson, T. Frejd, Org. Lett. 2000, 2, 1283.
37. J. P. Duan, C. H. Cheng, Organometallics 1995, 14, 1608.
38. E. J. Corey, Angew. Chem. 2002, 114, 1724
39. Angew. Chem. Int. Ed. 2002, 41, 1650
40. D. Li, G. Liu, Q. Hu, C. Wang, Z. Xi, Org. Lett. 2007, 9, 5433
41. D. Li, A. Shi, W.-X. Zhang, G. Liu, Z. Xi, Tetrahedron 2008, 64, 9895
42. D. A. Evans, J. S. Johnson, in Comprehensive Asymmetric Catalysis, Vol. III (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, New York, 1999, Chapter 33.1, pp. 1178-1235.
43. M. E. Jung, Synlett 1990, 186
44. M. E. Jung, J. Gervay, J. Am. Chem. Soc. 1991, 113, 224
45. M. E. Jung, G. Piizzi, Chem. Rev. 2005, 105, 1735
46. D. D. Sternbach, D. M. Rossana, K. D. Onan, J. Org. Chem. 1984, 49, 3427.
47. M. S. Bailey, B. J. Brisdon, D. W. Brown, K. M. Stark, Tetrahedron Lett. 1983, 24, 3037.
48. T. Kudoh, T. Mori, M. Shirahama, M. Yamada, T. Ishikawa, S. Saito, H. Kobayashi, J. Am. Chem. Soc. 2007, 129, 4939
49. M. Koerner, B. Rickborn, J. Org. Chem. 1989, 54, 6
50. R. A. Lee, Tetrahedron Lett. 1973, 14, 3333
51. G. A. Kraus, H. Sugimoto, Tetrahedron Lett. 1977, 18, 3929
52. M. Ihara, M. Toyota, K. Fukumoto, T. Kametani, Tetrahedron Lett. 1984, 25, 2167
53. Y. Tamura, M. Sasho, K. Nakagawa, T. Tsugoshi, Y. Kita, J. Org. Chem. 1984, 49, 473
54. M. Ihara, M. Suzuki, K. Fukumoto, T. Kametani, C. Kabuto, J. Am. Chem. Soc. 1988, 110, 1963
55. A. P. Marchand, P. Annapurna, W. H. Watson, A. Nagl, J. Chem. Soc. Chem. Commun. 1989, 281.
56. P. Hohenberg, W. Kohn, Phys. Rev. 1964, 136, B 864
57. W. Kohn, L. J. Sham, Phys. Rev. 1965, 140, A 1133.
58. Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215.
59. Gaussian 09, Revision A.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, A.. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.