An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective C-C bond cleavage of epoxides: Highly efficient synthesis of chiral furan derivatives

Chemical Communications

Volumn 50, Issue 78, 2014, Pages 11480-11483

  Chen, Weiliang ^a   Fu, Xuan ^a   Lin, Lili ^a   Yuan, Xiao ^a   Luo, Weiwei ^a   Feng, Juhua ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a  

^a Sichuan University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; LEWIS ACID; TETRACHLOROETHANE; TETRAHYDROFURAN DERIVATIVE; ALKYNE; CARBON; FURAN DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; CHEMICAL BOND; CHIRALITY; CYCLOADDITION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; STEREOSPECIFICITY; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKYNES; CARBON; CRYSTALLOGRAPHY, X-RAY; CYCLOADDITION REACTION; EPOXY COMPOUNDS; FURANS; HYDROGENATION; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84920070239     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc04182h     Document Type: Article

References (72)

1. Modern Allene Chemistry, ed. N. Krause and A. S. K. Hashmi, Wiley-VCH, Weinheim, Germany, 2004, vol. 1 and 2
2. B. M. Fraga, Nat. Prod. Rep., 1995, 12, 303
3. B. Esquivel, M. Flores, S. Hernández-Ortega, R. A. Toscano, T. P. Ramamoorthy, Phytochemistry, 1995, 39, 139
4. K. Katagiri, K. Tori, Y. Kimura, T. Yoshida, T. Nagasaki, H. Minato, J. Med. Chem., 1967, 10, 1149
5. A. Evidente, A. Andolfi, M. Fiore, E. Spanu, L. Maddau, A. Franceschini, F. Marras, A. Motta, J. Nat. Prod., 2006, 69, 671
6. F. Volz, N. Krause, Org. Biomol. Chem., 2007, 5, 1519
7. C.-X. Cui, H. Li, X.-J. Yang, J. Yang, X.-Q. Li, Org. Lett., 2013, 15, 5944
8. M. M. Faul, B. E. Huff, Chem. Rev., 2000, 100, 2407
9. B. H. Lipshutz, Chem. Rev., 1986, 86, 795
10. Natural Products Chemistry, ed. K. Nakanishi, T. Goto, S. Ito, S. Natori and S. Nozoe, Kodansha, Tokyo, 1974, vol. 1-3
11. The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, ed. T. Eicher and S. Hauptmann, Wiley-VCH, Weinheim, 2003
12. M. Maier, in Organic Synthesis Highlights II, ed. H. Waldmann, VCH, Weinheim, 1995, p. 231
13. R. Benassi, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon Press, Oxford, 1996, vol. 2, p. 259
14. J. W. Wesley, Polyether Antibiotics: Naturally Occurring Acid Ionophores, Marcel Dekker, New York, 1982, vol. I and II
15. F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod., 1999, 62, 504
16. R. D. Norcross, I. Paterson, Chem. Rev., 1995, 95, 2041
17. D. G Corley, R. Herb, R. E. Moore, P. J. Scheuer, V. J. Paul, J. Org. Chem., 1988, 53, 3644
18. S. Sakemi, T. Higa, C. W. Jefford, G. Bernardinelli, Tetrahedron Lett., 1986, 27, 4287
19. 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley Interscience, New York, 1984
20. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, ed. A. Padwa and W. H. Pearson, Wiley, New York, 2002
21. Cycloaddition Reactions in Organic Synthesis, ed. S. Kobayashi and K. A. Jørgensen, Wiley-VCH, Weinheim, Germany, 2002
22. A. Padwa, M. D. Weingarten, Chem. Rev., 1996, 96, 223
23. T. Graening, V. Bette, J. Neudörfl, J. Lex, H.-G. Schmalz, Org. Lett., 2005, 7, 4317
24. A. DeAngelis, M. T. Taylor, J. M. Fox, J. Am. Chem. Soc., 2009, 131, 1101
25. A. J. Skaggs, E. Y. Lin, T. F. Jamison, Org. Lett., 2002, 4, 2277
26. T. F. Schneider, J. Kaschel, D. B. Werz, Angew. Chem., Int. Ed., 2014, 53, 5504
27. P. D. Pohlhaus, S. D. Sanders, A. T. Parsons, W. Li, J. S. Johnson, J. Am. Chem. Soc., 2008, 130, 8642
28. A. T. Parsons, J. S. Johnson, J. Am. Chem. Soc., 2009, 131, 3122
29. A. G. Smith, M. C. Slade, J. S. Johnson, Org. Lett., 2011, 13, 1996
30. P. D. Pohlhaus, J. S. Johnson, J. Am. Chem. Soc., 2005, 127, 16014
31. F. Benfatti, F. de Nanteuil, J. Waser, Org. Lett., 2012, 14, 386
32. F. Benfatti, F. de Nanteuil, J. Waser, Chem. - Eur. J., 2012, 18, 4844
33. S. Xing, W. Pan, C. Liu, J. Ren, Z. Wang, Angew. Chem., Int. Ed., 2010, 49, 3215
34. A. B. Leduc, M. A. Kerr, Angew. Chem., Int. Ed., 2008, 47, 7945
35. S. D. Sanders, A. Ruiz-Olalla, J. S. Johnson, Chem. Commun., 2009, 5135
36. S. Haubenreisser, P. Hensenne, S. Schröder, M. Niggemann, Org. Lett., 2013, 15, 2262
37. P. D. Pohlhaus, J. S. Johnson, J. Org. Chem., 2005, 70, 1057
38. S. Kitagaki, M. Anada, O. Kataoka, K. Matsuno, C. Umeda, N. Watanabe, S.-I. Hashimoto, J. Am. Chem. Soc., 1999, 121, 1417
39. D. M. Hodgson, R. Glen, G. H. Grant, A. J. Redgrave, J. Org. Chem., 2003, 68, 581
40. N. Shimada, M. Anada, S. Nakamura, H. Nambu, H. Tsutsui, S. Hashimoto, Org. Lett., 2008, 10, 3603
41. J. Krishnamurthi, H. Nambu, K. Takeda, M. Anada, A. Yamano, S. Hashimoto, Org. Biomol. Chem., 2013, 11, 5374
42. K. Takeda, T. Oohara, N. Shimada, H. Nambu, S. Hashimoto, Chem. - Eur. J., 2011, 17, 13992
43. D. M. Hodgson, T. Brückl, R. Glen, A. H. Labande, D. A. Selden, A. G. Dossetter, A. J. Redgrave, Proc. Natl. Acad. Sci. U. S. A., 2004, 101, 5450
44. D. M. Hodgson, A. H. Labande, F. Y. T. M. Pierard, M. Á. Expósito Castro, J. Org. Chem., 2003, 68, 6153
45. H. Suga, D. Ishimoto, S. Higuchi, M. Ohtsuka, T. Arikawa, T. Tsuchida, A. Kakehi, T. Baba, Org. Lett., 2007, 9, 4359
46. G. Bentabed-Ababsa, S. Hamza-Reguig, A. Derdour, L. R. Domingo, J. A. Sáez, T. Roisnel, V. Dorcet, E. Nassar, F. Mongin, Org. Biomol. Chem., 2012, 10, 8434
47. M. Terada, Y. Toda, Angew. Chem., Int. Ed., 2012, 51, 2093
48. N. Shimada, T. Oohara, J. Krishnamurthi, H. Nambu, S. Hashimoto, Org. Lett., 2011, 13, 6284
49. J.-L. Zhou, Y. Liang, C. Deng, H. Zhou, Z. Wang, X.-L. Sun, J.-C. Zheng, Z.-X. Yu, Y. Tang, Angew. Chem., Int. Ed., 2011, 50, 7874
50. R. Liu, M. Zhang, J. Zhang, Chem. Commun., 2011, 47, 12870
51. Z. Chen, L. Wei, J. Zhang, Org. Lett., 2011, 13, 1170
52. T. Wang, C.-H. Wang, J. Zhang, Chem. Commun., 2011, 47, 5578
53. Z. Chen, Z. Tian, J. Zhang, J. Ma, J. Zhang, Chem. - Eur. J., 2012, 18, 8591
54. T. Wang, J. Zhang, Chem. - Eur. J., 2011, 17, 86
55. W. L. Chen, L. L. Lin, Y. F. Cai, Y. Xia, W. D. Cao, X. H. Liu, X. M. Feng, Chem. Commun., 2014, 50, 2161
56. R. Huisgen, Angew. Chem., Int. Ed., 1977, 16, 572
57. R. Huisgen, in Advances in Cycloaddition, ed. D. P. Curran, JAI Press Inc., Greenwich, 1988, vol. 1, pp. 1-32
58. G.-W. Wang, H.-T. Yang, P. Wu, C. B. Miao, Y. Xu, J. Org. Chem., 2006, 71, 4346
59. P. De March, R. Huisgen, J. Am. Chem. Soc., 1982, 104, 4952
60. R. Huisgen, P. De March, J. Am. Chem. Soc., 1982, 104, 4953
61. X. H. Liu, L. L. Lin, X. M. Feng, Acc. Chem. Res., 2011, 44, 574
62. W. L. Chen, Y. F. Cai, X. Fu, X. H. Liu, L. L. Lin, X. M. Feng, Org. Lett., 2011, 13, 4910
63. W. Li, X. H. Liu, X. Y. Hao, Y. F. Cai, L. L. Lin, X. M. Feng, Angew. Chem., Int. Ed., 2012, 51, 8644
64. W. Li, J. Wang, X. L. Hu, K. Shen, W. T. Wang, Y. Y. Chu, L. L. Lin, X. H. Liu, X. M. Feng, J. Am. Chem. Soc., 2010, 132, 8532
65. W. Li, X. H. Liu, F. Tan, X. Y. Hao, J. F. Zheng, L. L. Lin, X. M. Feng, Angew. Chem., Int. Ed., 2013, 52, 10883
66. A. Hassner, I. Namboothiri, Organic Syntheses Based on Name Reactions, Elsevier, Oxford, 3rd edn, 2011, p. 408
67. M. S. Xie, X. H. Liu, X. X. Wu, Y. F. Cai, L. L. Lin, X. M. Feng, Angew. Chem., Int. Ed., 2013, 52, 5604
68. J. Guo, S. X. Dong, Y. L. Zhang, Y. L. Kuang, X. H. Liu, L. L. Lin, X. M. Feng, Angew. Chem., Int. Ed., 2013, 52, 10245
69. X. H. Liu, L. L. Lin, X. M. Feng, Org. Chem. Front., 2014, 1, 298
70. M. P. Sibi, S. Manyem, Tetrahedron, 2000, 56, 8033
71. M. P. Sibi, G. Petrovic, Tetrahedron: Asymmetry, 2003, 14, 2879
72. K. Zheng, X. H. Liu, J. N. Zhao, Y. Yang, L. L. Lin, X. M. Feng, Chem. Commun., 2010, 46, 3771