Comparison of the relative reactivities of the triisopropylsilyl group with two fluorous analogs

Advanced Synthesis and Catalysis

Volumn 351, Issue 7-8, 2009, Pages 1035-1040

  Sancho, Amador Garcia ^a   Wang, Xiao ^a   Sui, Bin ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Fluorous chemistry; Protecting groups; Relative reactivity; Triisopropylsilyl group

Indexed keywords

EID: 66149131787     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900061     Document Type: Article

References (37)

1. W. Zhang, in: The Handbook of Fluorous Chemistry, (Eds.: J.A. Gladysz, D. P. Curran, I. T. Horvath), Wiley-VCH, Weinheim, 2004, pp 222-235.
2. a) R. E. Dolle, B. Le Bourdonnec, A. J. Goodman, G. A. Morales, C. J. Thomas, W. Zhang, J. Comb. Chem. 2008, 10, 753-802;
3. b) D. P. Curran, Aldrichimica Acta 2006, 39, 3-9.
4. A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf, D. P. Curran, Science 1997, 275, 823-826.
5. W. Zhang, D. P. Curran, Tetrahedron 2006, 62, 11837-11865.
6. a) Z. Y. Luo, Q. S. Zhang, Y. Oderaotoshi, D. P. Curran, Science 2001, 291, 1766-1769;
7. b) D. P. Curran, Q. S. Zhang, C. Richard, H. J. Lu, V. Gudipati, C. S. Wilcox, J. Am. Chem. Soc. 2006, 128, 9561-9573.
8. a) W. Zhang, J. Fluorine Chem. 2008, 129, 910-919;
9. b) D. P. Curran, in: The Handbook of Fluorous Chemistry, (Eds.: J.A. Gladysz, D. P. Curran, I. T. Horvath), Wiley-VCH, Weinheim, 2004, pp 101-127;
10. c) reverse fluorous FSE: M. Matsugi, D. P. Curran, Org. Lett. 2004, 6, 2717-2720.
11. a) P. Wipf, XT. Reeves, Tetrahedron Lett. 1999, 40, 4649-4652;
12. b) P. Wipf, J. T. Reeves, Tetrahedron Lett. 1999, 40, 5139-5142.
13. D. P. Curran, T. Furukawa, Org. Lett. 2002, 4, 2233-2235.
14. D. P. Curran, C. Ogoe, QSAR Comb. Sci. 2006, 25, 732-735.
15. a) A. Studer, D. P. Curran, Tetrahedron 1997, 55, 6681-6696;
16. A. Studer, P. Jeger, P. Wipf, D. P. Curran, J. Org. Chem. 1997, 62, 2917-2924;
17. b) S. Rover, P. Wipf, Tetrahedron Lett. 1999, 40, 5661-5610;
18. L. Manzoni, Chem. Commun. 2003, 2930-2931;
19. c) L. Manzoni, R. Castelli, Org. Lett. 2004, 6, 4195-4198;
20. d) S. Tripathi, K. Misra, Y. S. Sanghvi, Org. Prep. Proced. Int. 2005, 37, 257-263;
21. e) S. Fustero, A. G. Sancho, G. Chiva, J. F. Sanz-Cervera, C. del Pozo, J. L. Acena, J. Org. Chem. 2006, 71, 3299-3302.
22. a) Y. Lu, W. Zhang, e-EROS (Encycl. Reagents Org. Synth.), reagent number rn00424; fluorous TIPS tri-flate;
23. b) W Zhang, Z. Luo, C. H. T. Chen, D. P. Curran, J. Am. Chem. Soc. 2002, 124, 10443-10450;
24. c) Q. S. Zhang, A. Rivkin, D. P. Curran, J. Am. Chem. Soc. 2002, 124, 5774-5781;
25. d) F. Yang, J. J. Newsome, D. P. Curran, J. Am. Chem. Soc. 2006, 128, 14200-14205;
26. e) W.-H. Jung, S. Guyenne, C. Riesco-Fagundo, J. Man-cuso, S. Nakamura, D. P. Curran, Angew. Chem. 2008, 120, 1146-1149;
27. Angew. Chem. Int. Ed. 2008, 47, 1130-1133.
28. a) J. A. Gladysz, in: The Handbook of Fluorous Chemistry (Eds.: J. A. Gladysz, D. P. Curran, I. T. Horvath), Wiley-VCH, Weinheim, 2004, pp 41-55;
29. b) D. P. Curran, X. Wang, Q. S. Zhang, J. Org. Chem. 2005, 70, 3716-3719.
30. a) S.-W Yang, T.-Z. Chan, J. Terracciano, D. Loeben-berg, M. Patel, M. Chu, J. Antibiot. 2005, 58, 535-538;
31. b) X. Wang, PhD Thesis, University of Pittsburgh, 2009,
32. a) The fluorous silane precursors to make these compounds are commercially available from Fluorous Tech-nologies, Inc., www.fluorous.com;
33. b) DPC owns an equity interest in this company.
34. A. T. Khan, E. Mondal, Synlett 2003, 694-696.
35. Q. S. Zhang, D. P. Curran, Chem. Eur. J. 2005, 11, 4866-4880.
36. a) J. S. Kim, Y. J. Lim, K. S. Im, J. H. Jung, C. J. Shim, C. O. Lee, J. Hong, H. Lee, J. Nat. Prod. 1999, 62, 554-559;
37. b) Y. Seo, K. W. Cho, J.-R. Rho, J. Shin, C. J. Sim, Tetrahedron 1998, 54, 447-462.