Highly efficient access to Bi- and tricyclic ketals through gold-catalyzed tandem reactions of 4-acyl-1,6-diynes

Chemistry - A European Journal

Volumn 15, Issue 8, 2009, Pages 1830-1834

  Meng, Jia ^a   Zhao, Yu Long ^a   Ren, Chuan Qing ^a   Li, You ^a   Li, Zhu ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

Asymmetric synthesis; Cyclization; Domino reactions; Gold

Indexed keywords

CYCLIZATION; ELECTRON TRANSITIONS; ETHANOL; METHANOL; REACTION KINETICS;

ALLYL ALCOHOLS; ARYL GROUPS; ASYMMETRIC SYNTHESIS; CHIRAL CENTERS; CHIRAL INDUCTIONS; DIASTEREO SELECTIVITIES; DOMINO REACTIONS; REACTION SEQUENCES; TANDEM REACTIONS;

GOLD;

ALKYNE DERIVATIVE; FURAN DERIVATIVE; GOLD; KETONE;

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

CATALYSIS; CYCLIZATION; DIYNES; FURANS; GOLD; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 60749119748     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802304     Document Type: Article

References (90)

1. For reviews, see: a) D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378;
2. b) Z. Li. C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265;
3. c) E. Jiménez-Núñez, A.M. Echavarren, Chem. Rev. 2008, 108, 3326-3350;
4. d) N. Bongers. N. Krause, Angew. Chem. 2008, 120, 2208-2211;
5. Angew. Chem. Int. Ed. 2008, 47, 2178-2181;
6. e) N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395-3442;
7. f) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211;
8. g) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105;
9. Angew. Chem. Int. Ed. 2006, 45. 7896-7936;
10. h) A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519;
11. Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
12. i) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403;
13. j) E. Jiménez-Núñez. A. M. Echavarren, Chem. Commun. 2007, 333-346;
14. k) L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271-2296;
15. l) A. Hoffmann-Röder, N. Krause. Org. Biomol. Chem. 2005, 3, 387-391;
16. m) A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37. 1766-1775.
17. a) N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651;
18. b) G. Dyker, D. Hildebrandt, J. Liu, K. Merz, Angew. Chem. 2003, 115, 4536-4538;
19. Angew. Chem. Int. Ed. 2003, 42, 4399-4402;
20. c) T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164-11165;
21. d) J. Zhang, H.-G. Schmalz, Angew. Chem. 2006, 118, 6856-6859;
22. Angew. Chem. Int. Ed. 2006, 45, 6704-6707;
23. e) G. Li. X. Huang, L. Zhang, J. Am. Chem. Soc. 2008, 130, 6944-6945;
24. f) S. F. Kirsch, J. T. Binder, C. Liebert, H. Menz, Angew. Chem. 2006, 118, 6010-6013;
25. Angew. Chem. Int. Ed. 2006, 45, 5878-5880;
26. g) A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385;
27. Angew. Chem. Int. Ed. 2000, 39, 2285-2288;
28. h) Y. Liu, M. Liu, S. Guo, H. Tu, Y. Zhou, H. Gao, Org. Lett. 2006, 8, 3445-3448;
29. i) T. Yao, X. Zhang, R.C. Larock, J. Org. Chem. 2005, 70, 7679-7685;
30. j) T. Godet, C. Vaxelaire, C. Michel, A. Milet, P. Belmont, Chem. Eur. J. 2007, 13, 5632-5641
31. k) X. Yao, C.-J. Li, Org. Lett. 2006, 8, 1953-1955;
32. l) A. S. K. Hashmi, J. P. Weyrauch, W. Frey, J. W. Bats, Org. Lett. 2004, 6, 4391-4394.
33. S. Antoniotti, E. Genin, V. Michelet, J.-P. Genêt, J. Am. Chem. Soc. 2005, 127, 9976-9977.
34. For reviews, see: a) A. K. Ghosh, B. D. Chapsal, I. T. Weber, H. Mitsuya. Acc. Chem. Res. 2008, 41, 78-86;
35. b) R. E. Minto, C. A. Townsend, Chem. Rev. 1997, 97, 2537-2556;
36. c) P. F. Schuda, Top. Curr. Chem. 1980, 91, 75-111.
37. For selected reports, see: a) L.-G. Milroy, G. Zinzalla, G. Prencipe, P. Michel, S. V. Ley, M. Gunaratnam, M. Beltran, S. Neidle, Angew. Chem. 2007, 119, 2545-2548;
38. Angew. Chem. Int. Ed. 2007, 46, 2493-2496;
39. b) A. Diéguez- Vázquez, C. C. Tzschucke, W. Y. Lam, S. V. Ley, Angew. Chem. 2008, 120, 216-219;
40. Angew. Chem. Int. Ed. 2008, 47, 209-212;
41. c) M. Pirrung, Angew. Chem. 1985, 97, 1073-1074;
42. Angew. Chem. Int. Ed. Engl. 1985, 24, 1043-1044;
43. d) R. Roggenbuck, A. Schmidt, P. Eilbracht, Org. Lett. 2002, 4, 289-291.
44. For reviews on tandem reactions, see: a) Domino Reactions in Organic Synthesis (Eds.: L. F. Tietze. H. P. Bell, G. Brasche), Wiley-VCH, Weinheim, 2006;
45. b) D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590-1601;
46. Angew. Chem. Int. Ed. 2007, 46, 1570-1581;
47. c) K. C. Nicolaou, T. Montagnon, S. A. Snyder, Chem. Commun. 2003, 551-564;
48. d) A. Padwa. S. K. Bur, Tetrahedron 2007, 63, 5341-5378;
49. e) L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
50. For selected examples, see: a) X. Bi, D. Dong, O. Liu, W. Pan, L. Zhao, B. Li, J. Am. Chem. Soc. 2005, 127, 4578-4579;
51. b) C.-R. Piao, Y.-L. Zhao, X.-D. Han, O. Liu, J. Org. Chem. 2008, 73, 2264-2269;
52. c) J. Hu, O. Zhang, H. Yuan, Q. Liu, J. Org. Chem. 2008, 73, 2442-2445;
53. d) Y.-L. Zhao, D.-Z. Li, X.-D. Han, L. Chen, O. Liu, Adv. Synth. Catal. 2008, 350, 1537-1543;
54. e) L. Chen, Y.-L. Zhao, O. Liu, C. Chen, C.-R. Piao, J. Org. Chem. 2007, 72, 9259-9263;
55. f) J. Liu, M. Wang, B. Li, O. Liu, Y. Zhao, J. Org. Chem. 2007, 72, 4401 -4405;
56. g) Y.-L. Zhao, W. Zhang, S. Wang, O. Liu, J. Org. Chem. 2007, 72, 4985-4988;
57. h) F. Liang, D. Li, L. Zhang, J. Gao, Q. Liu, Org. Lett. 2007, 9, 4845-4848;
58. i) L. Zhao. F. Liang, X. Bi, S. Sun, Q. Liu, J. Org. Chem. 2006, 71, 1094-1098;
59. j) D. Dong, X. Bi, Q. Liu, F. Cong, Chem. Commun. 2005, 3580-3582;
60. k) Y. Li, F. Liang, X. Bi, Q. Liu, J. Org. Chem. 2006, 71, 8006-8010.
61. a) Z. Zhang, Q. Zhang, S. Sun, T. Xiong, Q. Liu, Angew. Chem. 2007, 119, 1756-1759;
62. Angew. Chem. Int. Ed. 2007, 46, 1726-1729;
63. b) Q. Zhang, Z. Zhang, Z. Yan, Q. Liu, T. Wang, Org. Lett. 2007, 9, 3651-3653;
64. c) Z. Zhang, Q. Zhang, Z. Yan, Q. Liu, J. Org. Chem. 2007, 72, 9808-9810;
65. d) W. Pan, D. Dong, K. Wang, J. Zhang, R. Wu, D. Xiang, Q. Liu, Org. Lett. 2007, 9, 2421 -2423.
66. For selected examples, see: a) B. M. Trost, M. T. Rudd, J. Am. Chem. Soc. 2003, 125, 11516-11517;
67. b) Y. Yamamoto, K. Hattori, H. Nishiyama, .A Am. Chem. Soc. 2006, 128, 8336-8340;
68. c) C. Gonzalez-Rodriguez, J. A. Varela, L. Castedo, C. Saá, J Am. Chem. Soc. 2007, 129, 12916-12917;
69. d) H. Kim, S.D. Goble, C. Lee, J. Am. Chem. Soc. 2007, 129, 1030-1031;
70. e) H.-Y. Jang, M. J. Krische, J. Am. Chem. Soc. 2004, 126, 7875-7880;
71. f) J. A. Varela, S. G. Rubín, C. González-Rodríguez, L. Castedo, C. Saá, J. Am. Chem. Soc. 2006, 128, 9262-9263;
72. g) Y. Yamamoto, K. Kinpara, R. Ogawa, H. Nishiyama, K. Itoh, Chem. Eur. J. 2006, 12, 5618-5631.
73. 2 =0.1610. CCDC 702106 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
74. 3. However, a complex mixture was observed.
75. 1H NMR spectra of products 3, it was found that the diastereoselectivity of the reaction is excellent and their diastereomers could not be observed.
76. 2=0.1153, CCDC 702107 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
77. a) N. Momiyama, M. W. Kanan, D. R. Liu, J. Am. Chem. Soc. 2007, 129, 2230-2231;
78. b) A. Das, H.-K. Chang, C.-H. Yang. R.-S. Liu, Org. Lett. 2008, 10, 4061-4064.
79. a) New Avenues to Efficient Chemical Synthesis. Emerging Technologies (Eds.: P. H. Seeberger, T. Blume), Springer. Heidelberg, 2007:
80. b) K. C. Nicolaou, E. W. Yue, T. Oshima in The New Chemistry (Ed.: N. Hall). Cambridge University Press. Cambridge. 2001. pp. 168-198;
81. c) L. F. Tietze, F. Hautner in Stimulating Concepts in Organic Chemistry (Eds.: F. Vögtle, J. F. Stoddart, M. Shibasaki). Wiley-VCH, Weinheim. 2000, pp. 38-64.
82. 2 = 0.1525. CCDC 705786 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
83. For reviews, see: a) K. Mori, Eur. J. Org. Chem. 1998, 1479-1489;
84. b) W. Francke, W. Schröder. Curr. Org. Chem. 1999, 3, 407-443;
85. c) K. Mori, Tetrahedron 1989, 45, 3233-3298.
86. a) S. D. Burke, N. Muller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829;
87. b) C. C. Marvin, E. A. Voight, S. D. Burke, Org. Lett. 2007, 9, 5357-5359;
88. c) E. A. Voight, H. Seradj, P. A. Roethle, S.D. Burke, Org. Lett. 2004, 6, 4045-4048.
89. K. Utimoto, Pure Appl. Chem. 1983, 55, 1845-1852.
90. L.-Z. Dai, M. Shi, Chem. Eur. J. 2008, 14, 7011-7018.