Straightforward and highly diastereoselective synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives promoted by BiCl3

Chemical Communications

Volumn 49, Issue 63, 2013, Pages 7085-7087

  Ma, Xiaofeng ^a,c   Tang, Qin ^a,c   Ke, Jun ^a,c   Zhang, Jichao ^a,c   Wang, Cong ^a,c   Wang, Haibo ^a,c   Li, Yuxue ^b   Shao, Huawu ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 CYCLOPROPANATED SUGAR; 2,2 DI SUBSTITUTED PERHYDROFURO[2,3 B ]PYRAN; ALKENE DERIVATIVE; ALLYLTRIMETHYLSILANE; BISMUTH CHLORIDE; BISMUTH DERIVATIVE; CARBOHYDRATE DERIVATIVE; CHLORIDE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; ETHER DERIVATIVE; FURAN; GLYCOSIDE; HYDROGEN; ORGANOSILICON DERIVATIVE; PYRAN; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; CYCLOADDITION; CYCLOPROPANATION; DIASTEREOISOMER; NUCLEAR OVERHAUSER EFFECT; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84882274673     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc42292e     Document Type: Article

References (39)

1. Y. Che, J. B. Gloer, J. A. Scott, D. Malloch, Tetrahedron Lett. 2004, 45, 6891.
2. M. Enomoto, T. Nakahata, S. Kuwahara, Tetrahedron, 2006, 62, 1102.
3. A. K. Ghosh, B. D. Chapsal, J. T. Weber, H. Mitsuya, Acc. Chem. Res. 2008, 41, 78.
4. A. K. Ghosh, D. D. Anderson, I. T. Weber, H. Mitsuya, Angew. Chem. Int. Ed. 2012, 51, 1778.
5. K. D. Eom, J. V. Raman, H. Kim, J. K. Cha, J. Am. Chem. Soc. 2003, 125, 5415.
6. X. F. Ma, Q. Tian, Q. Tang, J. Z. Zhao, H. W. Shao, Org. Lett. 2011, 13, 4276.
7. K. Ghosh, B. D. Chapsal, A. Baldridge, M. P. Steffey, D. E. Walters, Y. Koh, M. Amano, H. Mitsuya, J. Med. Chem. 2011, 54, 622.
8. A. K. Ghosh, D. D. Anderson, Future Med. Chem. 2011, 3, 1181.
9. B. Linclau, M. J. Jeffery, S. Josse, C. Tomassi, Org. Lett. 2006, 8, 5821.
10. R. Roggenbuck, A. Schmidt, P. Eilbracht, Org. Lett. 2002, 4, 289.
11. F. Alonso, D. Sánchez, T. Soler, M. Yus, Adv. Synth. Catal. 2008, 350, 2118.
12. F. Alonso, M. Rodríguez-Fernández, D. Sánchez, M. Yus, Eur. J. Org. Chem. 2011, 6459.
13. S. K. Yousuf, D. Mukherjee, L. Mallikharjunrao, S. C. Taneja, Org. Lett. 2011, 13, 576.
14. T. M. Pimpalpalle, S. R. Vidadala, S. Hotha, T. Linker, Chem. Commun. 2011, 47, 10434.
15. J. Yin, T. Linker, Tetrahedron, 2011, 67, 2447.
16. D. Sarkar, R. V. Venkateswaran, Tetrahedron, 2011, 67, 4559.
17. Y. J. Dai, F. Wu, Z. H. Zang, H. Z. You, H. G. Gong, Chem. Eur. J. 2012, 18, 808.
18. A. Ekomié, G. Lefévre, L. Fensterbank, E. Lacôte, M. Malacria, C. Ollivier, A. Jutand, Angew. Chem. Int. Ed. 2012, 51, 6942.
19. H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151.
20. M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117.
21. C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051.
22. F. De Simone, J. Waser, Synthesis, 2009, 3353.
23. Z. Lu, M. H. Shen, T. P. Yoon, J. Am. Chem. Soc. 2011, 133, 1162.
24. T. Tamaki, M. Ohashi, S. Ogoshi, Angew. Chem. Int. Ed. 2011, 50, 12067.
25. G. C. Lloyd-Jones, Angew. Chem. Int. Ed. 2006, 45, 6788.
26. T. F. Schneider, D. B. Werz, Org. Lett. 2011, 13, 1848.
27. M. Yu, B. L. Pagenkopf, Tetrahedron, 2005, 61, 321.
28. J. Yin, T. Linker, Org. Biomol. Chem. 2012, 10, 2351.
29. S. D. Haveli, P. R. Sridhar, P. Suguna, S. Chandrasekaran, Org. Lett. 2007, 9, 1331.
30. Q. Tian, L. Y. Xu, X. F. Ma, W. Zou, H. W. Shao, Org. Lett. 2010, 12, 540.
31. Q. Tian, L. Dong, X. F. Ma, L. Y. Xu, C. W. Hu, H. W. Shao, J. Org. Chem. 2011, 76, 1045.
32. H. W. Shao, Z. R. Wang, E. Lacroix, S. H. Wu, H. J. Jennings, W. Zou, J. Am. Chem. Soc. 2002, 124, 2130.
33. H. W. Shao, S. Ekthawatchai, S. H. Wu, W. Zou, Org. Lett. 2004, 6, 3497.
34. B. M. Wang, Y. Q. Tu, Acc. Chem. Res. 2011, 44, 1207.
35. O. Riant, J. Hannedouche, Org. Biomol. Chem. 2007, 5, 873.
36. D. J. Ramon, M. Yus, Curr. Org. Chem. 2004, 8, 149.
37. S. A. Yuzwa, M. S. Macauley, J. E. Heinonen, X. Y. Shan, R. J. Dennis, Y. A. He, G. E. Whitworth, K. A. Stubbs, E. J. McEachern, G. J. Davies, D. J. Vocadlo, Nat. Chem. Biol. 2008, 4, 483.
38. J. Y. Baek, B. Y. Lee, M. G. Jo, K. S. Kim, J. Am. Chem. Soc. 2009, 131, 17705.
39. H. Yamamoto, K. Futatsugi, Angew. Chem. Int. Ed. 2005, 44, 1924.