Synthesis of difurylmethane derivatives via the gold-catalyzed tandem cycloisomerization/dimerization of epoxide alkynes

Advanced Synthesis and Catalysis

Volumn 350, Issue 9, 2008, Pages 1275-1280

  Ji, Ke Gong ^a   Shen, Yong Wen ^a   Shu, Xing Zhong ^a   Xiao, Hui Quan ^a   Bian, Yong Jiang ^a   Liang, Yong Min ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Cycloisomerization; Dimerization; Epoxyalkynes; Furans; Gold

Indexed keywords

EID: 52049100220     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800130     Document Type: Article

References (61)

1. a) M. M. Bandurraga, F. William, S. F. Donovan, J. Clardy, J. Am. Chem. Soc. 1982, 104, 6463-6465;
2. b) J. A. Marshall, L. M. McNulty, D. Zou, J. Org. Chem. 1999, 64, 5193-5200;
3. c) J. A. Marshall, J. Liao, J. Org. Chem. 1998, 63, 5962-5970;
4. d) J. A. Marshall E. M. Wallace 1, J. Org. Chem. 1995, 60, 796-797.
5. a) S. A. Look, M. T. Burch, W. Fenical, Z. Qi-tai, J. Clardy, J. Org. Chem. 1985, 50, 5741-5746;
6. b) J. A. Marshall, W. J. DuBay, J. Org. Chem. 1994, 59, 1703-1708.
7. C. Frattini, C. Bicchi, C. Barettini, G. M. Nano, J. Agric. Food Chem. 1977, 25, 1238-1241.
8. a) A. Gandini, Adv. Polym. Sci. 1977, 25, 47;
9. b) Chem. Abstr. 1978, 88, 90046p.
10. a) A. V. Butin, V. T. Abaev, V. V. Mel'chin, A. S. Dmitriev, Tetrahedron Lett. 2005, 46, 8439-8441;
11. b) D. J. Macquarrie, S. J. Tavener, M. A. Harmer, Chem. Commun. 2005, 18, 2363-2365;
12. c) S. Onitsuka, H. Nishino, Tetrahedron 2003, 59, 755-765;
13. d) A. V. Gutnov, V. T. Abaev, A. V. Butin, A. S. Dmitriev, J. Org. Chem. 2001, 66, 8685-8686;
14. e) A. S. K. Hashmi, M. C. Blanco, Eur. J. Org. Chem. 2006, 19, 4340-4342;
15. f) V. Nair, N. Vidya, K. G. Abhilash, Tetrahedron Lett. 2006, 47, 2871-2873;
16. g) A. S. K. Hashmi, L. Schwarz, P. Rubenbauer, M. C. Blanco, Adv. Synth. Catal. 2006, 348, 705-708;
17. h) V. Nair, K. G. Abhilash, N. Vidya, Org. Lett. 2005, 7, 5857-5859;
18. i) T. Li, S. Cheng, J.-F. Lee, L.-Y. Jang, J. Mol. Catal. A: Chem. 2003, 198, 139-149;
19. j) V. Nair, N. Vidya, K. G. Abhilash, Synthesis 2006, 21, 3647-3653;
20. k) A. Riad, Z. Mouloungui, M. Delmas, A. Gaset, Synth. Commun. 1989, 19, 3169-3173;
21. l) I. G. Lovel, Yu. Sh. Gol'dberg, M. V. Shimanskaya, Khim. Geterotsikl. Soedin. 1989, 6, 746-749;
22. m) M.-E. Schwenter, P. Vogel, Chem. Eur. J. 2000, 6, 4091-4103.
23. a) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231;
24. b) J. A. Marshall, X. j. Wang, J. Org. Chem. 1991, 56 ,960-969.
25. a) S. F. Kirsch, Org. Biomol. Chem. 2006, 4, 2076-2080;
26. b) R. C. D. Brown, Angew. Chem. 2005, 117, 872-874;
27. Angew. Chem. Int. Ed. 2005, 44, 850-852;
28. c) T. Eicher, S. Hauptmann, A. Speicher, The Chemistry of Heterocycles, 2nd edn., Wiley-VCH, Weinheim, 2003, pp 57-62;
29. d) A. Jeevanandam, A. Ghule, Y.-C. Ling, Curr. Org. Chem. 2002, 6, 841-864;
30. e) S. Cacchi, G. Fabrizi, A. Goggiomani, Heterocycles 2002, 56, 613-632.
31. For recent reviews on gold catalysis, see: a) A. S. K. Hashmi, Angew. Chem. 2005, 117, 7150-7154;
32. Angew. Chem. Int. Ed. 2005, 44, 6990-6993;
33. b) A. Höffmann-Röder, N. Krause, Org. Biomol. Chem. 2005, 3, 387-391;
34. c) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105;
35. Angew. Chem. Int. Ed. 2006, 45, 7896-7936;
36. d) E. Jiménez-Núñez, A. M. Echavarren, Chem. Commun. 2007, 333-346;
37. e) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403;
38. f) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211.
39. a) Y. Liu, F. Song, Z. Song, M. Liu, B. Yan, Org. Lett. 2005, 7, 5409-5412;
40. b) A. S. K. Hashmi, P. Sinha, Adv. Synth. Catal. 2004, 346, 432-438;
41. c) A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385;
42. Angew. Chem. Int. Ed. 2000, 39, 2285-2288;
43. d) C.-Y. Zhou, P. W. H. Chan, C.-M. Che, Org. Lett. 2006, 8, 325-328;
44. e) J. Zhang, H.-G. Schmalz, Angew. Chem. 2006, 118, 6856-6859;
45. Angew. Chem. Int. Ed. 2006, 45, 6704-6707;
46. f) T. Yao, X. Zhang, R. C. Larock, J. Org. Chem. 2005, 70, 7679-7685;
47. g) T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164-11165;
48. h) X. Liu, Z. Pan, X. Shu, X. Duan, Y. Liang, Synlett 2006, 1962-1964;
49. i) X.-Z. Shu, X.-Y. Liu, H.-Q. Xiao, K.-G. Ji, L.-N. Guo, Y.-M. Liang, Adv. Synth. Catal. 2008, 350, 243-248.
50. X.-Z. Shu, X.-Y. Liu, H.-Q. Xiao, K.-G. Ji, L.-N. Guo, C.-Z. Qi, Y.-M. Liang, Adv. Synth. Catal. 2007, 349, 2493-2498.
51. syn/anti Mixtures of the substrate esters of 1-alkynyl-2,3-epoxy alcohols were used. The reaction products were not found to be affected by the stereochemical configuration of the substrate. For a full explanation and definition of the terms syn and anti as used herein see: C. M. Marson, D. W. M. Benzies, A. D. Hobson, Tetrahedron 1991, 47, 5491-5506.
52. Similar intermediates have been reported by Sarpong, see: a) B. G. Pujanauski, B. A. Bhanu Prasad, R. Sarpong, J. Am. Chem. Soc. 2006, 128, 6786-6787;
53. for the transition metal-catalyzed oxonium ion formation, see: b) N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651;
54. c) N. Asao, T. Nogami, S. Lee, Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 10921-10925;
55. d) N. Asao, H. Aikawa, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 7458-7459;
56. e) J. Zhu, A. R. Germain, J. A. J. Porco, Angew. Chem. 2004, 116, 1259-1263;
57. Angew. Chem. Int. Ed. 2004, 43, 1239-1243;
58. f) K. Sato, S. S. Yudha, N. Asao, Y. Yamamoto, Synthesis 2004, 9, 1409-1412;
59. g) H. Kusama, H. Funami, M. Shido, Y. Hara, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 2709-2716.
60. 2O, 2-(α-hydroxyalkyl)furans G might lead to the formation of the cation intermediates H, which undergo the Friedel-Crafts-type reaction to afford the difurylmethanes I. (Chemical Equation Presented)
61. Asimilar mechanism has been reported by Marson, see: C. M. Marson, J. Campbell, Tetrahedron Lett. 1997, 38, 7785-7788.