Highlights of applications in synthesis and catalysis: 10.6 fluorous scavengers

Handbook of Fluorous Chemistry

Volumn , Issue , 2005, Pages 236-246

  Lindsley, Craig W ^a   Leister, William H ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Fluorous chemistry; Fluorous scavengers

Indexed keywords

FLUOROUS;

EID: 84958649232     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527603905.ch10f     Document Type: Chapter

References (34)

1. Thompson, L. A.; Ellman, J. A. Chem Rev. 1996, 96, 555-600.
2. Dorwald, F. Z. Organic Synthesis on Solid Phase, Wiley-VCH: Weinheim, 2000.
3. Burgess, K. Solid Phase Organic Synthesis, Wiley: New York, 2000 and references therein.
4. Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
5. Hermkens, P. H. H.; Ottenheijm, H. C.; Rees, D. Tetrahedron 1996, 52, 4527-4554.
6. Sucholeiki, I. Ed. High-Throughput Organic Synthesis, Marcel Dekker, New York, 2000 and references therein.
7. Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26.
8. Gayo, L. M. Biotechnol. Bioeng. 1998, 61, 95-106.
9. For an excellent review on workup procedures developed for SPPS see: Cork, D.; Hird, N. Drug Discovery Today 2002, 7, 56-63.
10. Booth, J. R.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882-4886.
11. Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. Tetrahedron Lett. 1997, 38, 3357-3360.
12. Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101-106.
13. Showalter, H. D. Chemtracts-Org. Chem. 1997, 10, 673-676.
14. Polymer-supported reagents and scavengers are available from Aldrich, Fluka, Argonaut Technologies, Advanced ChemTech and NovaBiochem to list just a few of the suppliers.
15. Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell, J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357-3360.
16. Suto, M. J.; Gayo-Fung, L. M.; Palanki, M. S. S.; Sullivan, R. Tetrahedron Lett. 1997, 38, 7579-7962.
17. Struder, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826.
18. Curran, D. P. Synlett 2001, 1488- 1496.
19. Curran, D. P. Pure Appl. Chem. 2000, 72, 1649-1653.
20. Lou, Z. Y.; Williams, J.; Read, R. W.; Curran, D. P. J. Org. Chem. 2001, 66, 4261-4266.
21. Commercially available FSPE cartridges, FluoroFlashTM SPE, from Fluorous Technolgies Incorporated, www.fluorous.com.
22. Curran, D. P. Chemtracts-Org. Chem. 1996, 9, 75-80.
23. Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480-6486.
24. Curran, D. P. Hadida, S.; Kim, S.-Y.; Luo, Z. J. Am. Chem. Soc. 1999, 121, 6607-6615.
25. Linclau, B.; Sing, A. K.; Curran, D. P. J. Org. Chem. 1999, 64, 2835-2842.
26. Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391-9395.
27. Curran, D. P.; Hadida, S.; Kim, S. Y. Tetrahedron 1999, 55, 8997-9006.
28. Zhang, W.; Curran, D. P.; Chen, C. H.-T. Tetrahedron 2002, 58, 3871-3875.
29. Lindsley, C. W.; Zhao, Z.; Leister, W. H. Tetrahedron Lett. 2002, 43, 4225-4228.
30. Lindsley, C. W.; Zhao, Z.; Leister, W. H.; Strauss, K. A. Tetrahedron Lett. 2002, 43, 6319-6323.
31. Zhang, W.; Chen, C. H.-T.; Nagashima, T. Tetrahedron Lett. 2003, 44, 2065-2068.
32. Fluorous reagents are commercially available from a number of vendors including: Aldrich, Lancaster, TCI America and Fluorous Technologies Incorporated (FTI). Fluorous separation media is available from FTI and Silicycle.
33. Lindsley, C. W.; Zhao, Z. unpublished results from Merck Research Laboratories.
34. Commercially available from Biotage, Inc., www.biotage.com.