Highly efficient and diastereoselective synthesis of 1,3-oxazolidines featuring a palladium-catalyzed cyclization reaction of 2-butene-1,4-diol derivatives and imines

Tetrahedron Letters

Volumn 51, Issue 39, 2010, Pages 5131-5133

  Chen, Dongxu ^a   Chen, Xiaoyi ^a   Du, Taiping ^a   Kong, Lichun ^a   Zhen, Renwei ^a   Zhen, Shaocheng ^a   Wen, Yihang ^a   Zhu, Gangguo ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BUTANEDIOL; AMINOALCOHOL; IMINE; OXAZOLIDINE DERIVATIVE; PALLADIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ENZYME SUBSTRATE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 77956225392     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.087     Document Type: Article

References (33)

1. F. Fache, E. Schulz, M.L. Tommasino, and M. Lemaire Chem. Rev. 100 2000 2159
2. A. Deiters, and S.F. Martin Chem. Rev. 104 2004 2199
3. T. Haack, and M. Mutter Tetrahedron Lett. 33 1992 1589
4. C. Agami, and F. Couty Eur. J. Org. Chem. 2004 677
5. J. Wang, F.D. Rochon, Y. Yang, L. Hua, and M.M. Kayser Tetrahedron: Asymmetry 18 2007 1115
6. Y.-F. Kang, R. Wang, L. Liu, C.-S. Da, W.-J. Yan, and Z.Q. Xu Tetrahedron Lett. 46 2005 863
7. A. Padwa, and W. Dent J. Org. Chem. 52 1987 235
8. A. Hosomi, Y. Miyashiro, R. Yoshida, Y. Tominaga, T. Yanagi, and M. Hojo J. Org. Chem. 55 1990 5308
9. C. Wittland, M. Arend, and N. Risch Synthesis 1996 367
10. S.-H. Lee, J. Yang, and T.-D. Han Tetrahedron Lett. 42 2001 3487
11. T. Hayashi, A. Yamamoto, and Y. Ito Tetrahedron Lett. 29 1988 99
12. J.-G. Shim, and Y. Yamamoto Tetrahedron Lett. 40 1999 1053
13. G.A. Inman, D.C.D. Butler, and H. Alper Synlett 2001 914
14. V.K. Yadav, and V. Sriramurthy J. Am. Chem. Soc. 127 2005 16366
15. B. Kang, A.W. Miller, S. Goyal, and S.T. Nguyen Chem. Commun. 2009 3928
16. C. Huo, R. Wei, W. Zhang, L. Yang, and Z.-L. Liu Synlett 2005 161
17. V. Sriramurthy, G.A. Barcan, and O. Kwon J. Am. Chem. Soc. 129 2007 12928
18. S. Purushothaman, and R. Raghunathan Tetrahedron Lett. 50 2009 6848
19. M.R. Mohammadizadeh, and N. Firoozi Tetrahedron Lett. 51 2010 2467
20. D.J. Michaelis, C.J. Shaffer, and T.P. Yoon J. Am. Chem. Soc. 129 2007 1866
21. D.J. Michaelis, M.A. Ischay, and T.P. Yoon J. Am. Chem. Soc. 130 2008 6610
22. K.S. Williamson, and T.P. Yoon J. Am. Chem. Soc. 132 2010 4570
23. G. Zhu, and Z. Zhang Org. Lett. 5 2003 3645
24. G. Zhu, and Z. Zhang Org. Lett. 6 2004 4041
25. S.C. Bergmeier Tetrahedron 56 2000 2561
26. G. Liu, and S.S. Stahl J. Am. Chem. Soc. 128 2006 7179
27. R.G. Wilkinson, R.G. Shepherd, J.P. Thomas, and T.C. Baughn J. Am. Chem. Soc. 83 1961 2212
28. S.-L. You, X.-Z. Zhu, Y.-M. Luo, X.-L. Hou, and L.-X. Dai J. Am. Chem. Soc. 123 2001 7471
29. T. Graening, and H.-G. Schmalz Angew. Chem., Int. Ed. 42 2003 2580
30. L.-X. Dai, T. Tu, S.-L. You, W.-P. Deng, and X.-L. Hou Acc. Chem. Res. 36 2003 659
31. S.-L. You, and L.-X. Dai Angew. Chem., Int. Ed. 45 2006 5246
32. J.-H. Xie, and Q.-L. Zhou Acc. Chem. Res. 41 2008 581
33. M. Diéguez, and O. Pmies Acc. Chem. Res. 43 2010 312