Fluorous electrophilic scavengers for solution-phase parallel synthesis

Tetrahedron Letters

Volumn 44, Issue 10, 2003, Pages 2065-2068

  Zhang, Wei ^a   Chen, Christine Hiu Tung ^a   Nagashima, Tadamichi ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; AMINE; ISOCYANATE; SCAVENGER; THIOUREA; UREA;

ARTICLE; DEVICE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE EXTRACTION; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

LETHRINIDAE;

EID: 0037416843     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00178-3     Document Type: Article

References (30)

1. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
2. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
3. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
4. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
5. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
6. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
7. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
8. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
9. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
10. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
11. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
12. Representative reviews: (a) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101; (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217; (c) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18; (d) Flynn, D. Med. Res. Rev. 1999, 19, 408; (e) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320; (f) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324; (g) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815; (h) Hodges, J. C. Synlett 2000, 152; (i) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035; (j) Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224; (k) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 650; (l) Yoshida, J.-I.; Itami, K. Chem. Rev. 2002, 102, 3693.
13. Curran D.P. Chemtracts-Org. Chem. 9:1996;75.
14. Curran D.P. Angew. Chem., Int. Ed. Engl. 37:1998;1175.
15. Curran D.P. Stoddard F., Reinhoudt D., Shibasaki M. Stimulating Concepts in Chemistry. 2000;25 Wiley-VCH, New York.
16. Curran D.P., Hadida S., Studer A., He M., Kim S.-Y., Luo Z., Larhed M., Hallberg M., Linclau B. Fenniri H. Combinatorial Chemistry: A Practical Approach. 2:2001;327 Oxford University Press, Oxford.
17. Curran D.P. Synlett. 2001;1488.
18. Zhang W., Curran D., Chen C.H.-T. Tetrahedron. 58:2002;3871.
19. For related fluorous scavenger work, see: (a) Lindsley, C. W.; Zhao, Z.; Leister, W. H. Tetrahedron Lett. 2002, 43, 4225; (b) Lindsley, C. W.; Zhao, Z.; Leister, W. H. Strauss, K. A. Tetrahedron Lett. 2002, 43, 6319.
20. For related fluorous scavenger work, see: (a) Lindsley, C. W.; Zhao, Z.; Leister, W. H. Tetrahedron Lett. 2002, 43, 4225; (b) Lindsley, C. W.; Zhao, Z.; Leister, W. H. Strauss, K. A. Tetrahedron Lett. 2002, 43, 6319.
21. Early work on fluorous quenching combined with liquid-liquid extraction, see: (a) Curran, D. P.; Hadida, S.; Kim, S. Y.; Luo, Z. Y. J. Am. Chem. Soc. 1999, 121, 6607; (b) Linclau, B.; Singh, A. K.; Curran, D. P. J. Org. Chem. 1999, 64, 2835; (c) Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391.
22. Early work on fluorous quenching combined with liquid-liquid extraction, see: (a) Curran, D. P.; Hadida, S.; Kim, S. Y.; Luo, Z. Y. J. Am. Chem. Soc. 1999, 121, 6607; (b) Linclau, B.; Singh, A. K.; Curran, D. P. J. Org. Chem. 1999, 64, 2835; (c) Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391.
23. Early work on fluorous quenching combined with liquid-liquid extraction, see: (a) Curran, D. P.; Hadida, S.; Kim, S. Y.; Luo, Z. Y. J. Am. Chem. Soc. 1999, 121, 6607; (b) Linclau, B.; Singh, A. K.; Curran, D. P. J. Org. Chem. 1999, 64, 2835; (c) Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391.
24. Polymer-supported isatoic anhydride: Coppola G.M. Tetrahedron Lett. 39:1998;8233.
25. Polymer-supported isocyanate: (a) Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dessman, B. A.; Hahn, P. Tetrahedron Lett. 1996, 37, 7193; (b) Booth, J. R.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882.
26. Polymer-supported isocyanate: (a) Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dessman, B. A.; Hahn, P. Tetrahedron Lett. 1996, 37, 7193; (b) Booth, J. R.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882.
27. Ouari O., Polidori A., Pucci B., Tordo P., Chalier F. J. Org. Chem. 64:1999;3554.
28. 2O (80:20) for the next round of SPE. The cartridge can be reused up to 10 times.
29. ++H, 100).
30. Fluorous isatoic anhydride 1, isocyanate 2, and FluoroFlash™ SPE cartridges are available from Fluorous Technologies, Inc. http://www.fluorous.com.