Phase-switch synthesis with boronic acids as productive tags

Journal of Combinatorial Chemistry

Volumn 9, Issue 2, 2007, Pages 193-196

  Mothana, Sam ^a   Chahal, Navjot ^a   Vanneste, Sébastien ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; PEPTIDE;

ARTICLE; CHEMISTRY; SYNTHESIS;

BORONIC ACIDS; PEPTIDES;

EID: 34047241282     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc060149s     Document Type: Article

References (39)

1. (a) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196.
2. (b) Yoshida, J.-i.; Itami, K. Chem. Rev. 2002, 102, 3693-3716.
3. (c) Tzschucke, C. C.; Markert, C.; Bannwarth, W.; Roller, S.; Hebel, A.; Haag, R. Angew. Chem., Int. Ed. 2002, 41, 3964-4000.
4. (a) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S. Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826.
5. (b) For a review of fluorous synthesis, see: Zhang, W. Tetrahedron 2003, 59, 4475-4489.
6. (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-510.
7. (b) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546-554.
8. (c) Janda, K. D.; Dickerson, T. J.; Reid, N. N. Chem. Rev. 2002, 102, 3325-3344.
9. (d) Wilcox, C. S.; Turkyilmaz, S. Tetrahedron Lett. 2005, 46, 1827-1829.
10. (a) Ley, S. V.; Massi, A.; Rodriguez, F.; Horwell, D. C.; Lewthwaite, R. A.; Pritchard, M. C.; Reid, A. M. Angew. Chem., Int. Ed. 2001, 40, 1053-1055.
11. (b) Lepore, S. D. Tetrahedron Lett. 2001, 42, 6437-6439.
12. (c) Siu, J.; Baxendale, I. R.; Lewthwaite, R. A.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 3140-3160.
13. (a) Zhang, S.; Fukase, K.; Kusumoto, S. Tetrahedron Lett. 1999, 40, 7479-7483.
14. (b) Zhang, S.-Q.; Fukase, K.; Izumi, M.; Fukase, Y.; Kusumoto, S. Synlett 2001, 590-596.
15. (a) Barrett, A. G. M.; Hopkins, B. T.; Kobberling, J. Chem. Rev. 2002, 102, 3301-3324.
16. (b) Harred, A. M.; Zhang, M. J.; Vedantham, P.; Mukherjee, S.; Herpel, R. H.; Flynn, D. L.; Hanson, P. R. Aldrichim. Acta 2005, 38, 3-16.
17. (a) Kanie, O.; Barresi, F.; Ding, Y. L.; Labbe, J.; Otter, A.; Forsberg, L. S.; Ernst, B.; Hindsgaul, O. Angew. Chem., Int. Ed. Engl. 1995, 34, 2720-2722.
18. (b) Hay, A. M.; Hobbs-Dewitt, S.; MacDonald, A. A.; Ramage, R. Synthesis 1999, 1979.
19. (c) Perrier, H.; Labelle, M. J. Org. Chem. 1999, 64, 2110-2113.
20. (d) Warmus, J. S.; da Salva, M. I. Org. Lett. 2000, 2, 1807-1809.
21. (e) Itami, K.; Nokami, T.; Yoshida, J.-I. Angew. Chem., Int. Ed. 2001, 40, 1074-1076.
22. (f) Bosanac, T.; Yang, J. M.; Wilcox, C. S. Angew. Chem., Int. Ed. 2001, 40, 1875-1879.
23. (g) Itami, K.; Mitsudo, K.; Nokami, T.; Kamei, T.; Koike, T.; Yoshida, J.-Y. J. Organomet. Chem. 2002, 653, 105-113.
24. (h) Bosanac, T.; Wilcox, C. S. J. Am. Chem. Soc. 2002, 124, 4194-4195.
25. (i) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345-3384.
26. (j) Lan, P.; Porco, J. A., Jr.; South, M. S.; Parlow, J. J. J. Comb. Chem. 2003, 5, 660-669.
27. (k) Li, X.; Abell, C.; Congreve, M. S.; Warrington, B. H.; Ladlow, M. Org. Biomol. Chem. 2004, 2, 989-998.
28. Poupon, J.-C; Boezio, A. A.; Charette, A. B. Angew. Chem., Int. Ed. 2006, 45, 1415-1420.
29. Hall, D. G., Ed. Boronlc Acids - Preparation and Applications in Organic Synthesis and Medicine; Wiley-VCH: Weinheim, Germany, 2005.
30. Hall, D. G.; Tailor, J.; Gravel, M. Angew. Chem., Int. Ed. 1999, 38, 3064-3067.
31. Gravel, M.; Thompson, K. A.; Zak, M.; Berube, C.; Hall, D. G. J. Org. Chem. 2002, 67, 3-15.
32. Pourbaix, C.; Carreaux, F.; Carboni, B.; Deleuze, H. Chem. Commun. 2000, 1275-1276.
33. 2O/THF solution (3x). The filtrates are combined, concentrated under reduced pressure, and dried under high vacuum to yield the product.
34. Liu, K.-C.; Shelton, B. R.; Howe, R. K. J. Org. Chem. 1980, 45, 3916-3918.
35. Weidner-Wells, M. A.; Fraga-Spano, S. A.; Turchi, I. J. J. Org. Chem. 1998, 63, 6319-6328.
36. A related cross-coupling/detagging was reported on a fluorous boronate, see: Chen, D.; Qing, F.-L; Huang, Y. Org. Lett. 2002, 4, 1003-1005. In this case, however, the required fluorous tag is not commercial, needs to be prepared in several steps, and does not circumvent the attachment step as with the free boronic acids used in the DEAM-PS system.
37. For an approach based on homogeneous polyglycerol, which also requires a separate immobilization operation, see: Hebel, A.; Haag, R. J. Org. Chem. 2002, 67, 9452-9455.
38. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446.
39. For a microwave-promoted procedure, see: McLean, N. J.; Tye, H.; Whittaker, M. Tetrahedron Lett. 2004, 45, 993-995.