Fluorous benzaldehyde-based synthesis of biaryl-substituted oxazabicyclo[3.3.1]nonanes

Green Chemistry

Volumn 13, Issue 4, 2011, Pages 847-849

  Ding, Shan ^a   Le Nguyen, Minhgiao ^a   Xu, Tao ^a   Zhang, Wei ^a  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79953813823     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c0gc00725k     Document Type: Article

References (36)

1. M. Demeunynck and A. Tatibouet, in Progress in Heterocyclic Chemistry; ed. G. W. Gribble and T. L. Cilchrist, Pergamon, Oxford, 1999, vol. 11, pp. 1–20.
2. R. A. Johnson R. R. Gorman R. J. Wnuk N. J. Crittenden J. W. Aiken J. Med. Chem. 1993 36 3202-3206.
3. C. Bailly W. Laine M. Demeunynck J. Lhomme Biochem. Biophys. Res. Commun. 2000 273 681-685.
4. M. Harmata M. Kahraman Tetrahedron: Asymmetry 2000 11 2875-2879.
5. H. U. Blaser H. P. Jalett W. Lottenbach M. Studer J. Am. Chem. Soc. 2000 122 12675-12682.
6. J. Tröger J. Prakt. Chem. 1887 36 225-245.
7. J. S. Chen W. H. Watson J. Kagan D. A. Agdeppa S.-A. Chen Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1978 34 3627-3630.
8. P. Molina A. Arques A. Tarraga M. del Rosario Obon C. Foces-Foces N. Jagerovic J. Elguero Tetrahedron 1998 54 997-1004.
9. J. T. Wang Y.-X. Liao P.-Y. Kuo Y.-H. Gau D.-Y. Yang Synlett 2006 2791-2794.
10. J.-T. Lai P.-Y. Kuo Y.-H. Gau D.-Y. Yang Tetrahedron Lett. 2007 48 7796-7800.
11. D.-Y. Yang Y.-S. Chen P.-Y. Kuo J.-T. Lai C.-M. Jiang C.-H. Lai Y.-H. Liao P.-T. Chou Org. Lett. 2007 9 5287-5290.
12. J. T. Lai P. S. Shieh W. H. Huang D. Y. Yang J. Comb. Chem. 2008 10 381-386.
13. J. T. Lai Y. J. Yang J. H. Lin Y. J. Yang J. H. Lin D. Y. Yang Synlett 2010 111-114.
14. C.-H. Lin J.-R. Chen D.-Y. Yang J. Comb. Chem. 2010 12 119-124.
15. W. Zhang Green Chem. 2009 11 911-920.
16. W. Zhang Chem. Rev. 2009 109 749-795.
17. W. Zhang Comb. Chem. High Throughput Screening 2007 10 219-229.
18. W. Zhang Chem. Rev. 2004 104 2531-2556.
19. Y. Lu W. Zhang QSAR Comb. Sci. 2004 23 827-835.
20. W. Zhang C. H.-T Chen Tetrahedron Lett. 2005 46 1807-1810.
21. H. Zhou A. Liu X. Li X. Ma W. Feng W. Zhang B. Yan J. Comb. Chem. 2008 10 303-312.
22. A. Liu H. Zhou G. Su W. Zhang B. Yan J. Comb. Chem. 2009 11 1083-1093.
23. H. Zhou W. Zhang B. Yan J. Comb. Chem. 2010 12 206-214.
24. W. Zhang D. P. Curran Tetrahedron 2006 62 11837-11865.
25. W. Zhang, in Microwave Methods in Organic Synthesis; Topics Curr. Chem., vol. 266, ed. M. Larhed and K. Olofsson, Springer, 2006, pp. 145–166.
26. W. Zhang Y. Lu C. H.-T Chen Mol. Diversity 2003 7 199-202.
27. W. Zhang T. Nagashima Y. Lu C. H.-T Chen Tetrahedron Lett. 2004 45 4611-4613.
28. W. Zhang T. Nagashima J. Fluorine Chem. 2006 127 588-591.
29. Synthesis of fluorous benzaldehydes, see ref. 11a.
30. 2-promoted synthesis of tetrahydroquinoline, see: S. Yamazaki M. Takebayashi K. Miyazaki J. Org. Chem. 2010 75 1188-1196.
31. Fluorous SPE cartridges are available from Fluorous Technologies, Inc. (www.fluorous.com) and Silicycle (www.silicycle.com).
32. +.
33. +.
34. W. Zhang C. H.-T Chen Y. Lu T. Nagashima Org. Lett. 2004 6 1473-1476. See also ref. 11a.
35. +.
36. P. J. H. Scott I. B. Campbell P. G. Steel J. Fluorine Chem. 2005 126 1196-1201.