Solid-Phase organic synthesis of difluoroalkyl entities using a novel fluorinating cleavage strategy: Part 2. synthesis of three small gem-difluorinated compound libraries using a dithiane linker

Journal of Combinatorial Chemistry

Volumn 11, Issue 6, 2009, Pages 982-1006

  Wiehn, Matthias S ^a   Fürniss, Daniel ^a   Bräse, Stefan ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DITHIANE; FLUORINATED HYDROCARBON; QUINOLIZINE DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; MOLECULAR LIBRARY; STEREOISOMERISM; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; QUINOLIZINES; SMALL MOLECULE LIBRARIES; STEREOISOMERISM; SULFUR COMPOUNDS;

EID: 70449382069     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9000899     Document Type: Article

References (21)

1. Wiehn, M. S.; Lindell, S. D.; Bräse, S. J. Comb. Chem. 2009, DOI: 10.1021/cc900090p.
2. Wiehn, M. S.; Lindell, S. D.; Bräse, S. Angew. Chem., Int. Ed. 2008, 47, 8120-8122.
3. For biaryl libraries, see: Wade, J. V.; Krueger, C. A. J. Comb. Chem. 2003, 5, 267-272.
4. Nilsson, M.; Norm, T. Acta Chem. Scand. 1963, 17, 11571159.
5. Kokubun, T.; Harborne, J. B.; Eagles, J.; Waterman, P. G. Phytochemistry 1995, 40, 57-59.
6. Shibata, Y. Arzneim.-Forsch. 1980, 30, 1074-1076.
7. Tamura, Y.; Yoshimoto, Y.; Kunimoto, K.; Tada, S.; Tomita, T.; Wada, T.; Seto, E.; Murayama, M.; Shibata, Y. J. Med. Chem. 1977, 20, 709-714.
8. Wilson, F.; Reid, A.; Reader, V.; Harrison, R. J.; Sunose, M.; Hernandez-Perni, R.; Major, J.; Boussard, C.; Smelt, K.; Taylor, J.; Le Formal, A.; Cansfield, A.; Burckhardt, S. (Cellzome (UK) Ltd., U.K.) Eur. Pat. Appl. EP 1849762 Al 20071031, 2007.
9. For a review of Suzuki coupling in SPOS, see: (a) Bräse, S.; Kirchhoff, J. H.; Köbberling, J. Tetrahedron 2003, 59, 885939. For pioneering studies, see:
10. (b) Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169-5171.
11. (c) Knepper, K.; Vanderheiden, S.; Bräse, S. Eur. J. Org. Chem. 2006, 1886-1898.
12. (d) Gil, C.; Schwögler, A.; Bräse, S. J. Comb. Chem. 2004, 6, 38-42.
13. (e) Kivrakidou, O.; Bräse, S.; Hülshorst, F.; Griebenow, N. Org. Lett. 2004, 6, 1143-1146.
14. For an alternative approach, see: Rozen, S.; Lerman, O. J. Org. Chem. 1993, 58, 239-240.
15. Choi, H. Y.; Chi, D. Y. Org. Lett. 2003, 5, 411-414.
16. King, A. O.; Corley, E. G.; Anderson, R. K.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J.; Xiang, Y. B.; Belley, M.; Leblanc, Y. J. Org. Chem. 1993, 58, 3731-3735.
17. Palomer, A.; Pascual, J.; Cabre, M.; Borras, L.; Gonzalez, G.; Aparici, M.; Carabaza, A.; Cabre, F.; Garcia, M. L.; Mauleon, D. Bioorg. Med. Chem. Lett. 2002, 12, 533-537.
18. Minta, E.; Boutonnet, C.; Boutard, N.; Martinez, J.; Rolland, V. Tetrahedron Lett. 2005, 46, 1795-1797.
19. For application of A1Me3-mediated amidation reactions to solution phase peptide synthesis, see: Martin, S. F.; Dwyer, M. P.; Lynch, L. L. Tetrahedron Lett. 1998, 39, 1517-1520.
20. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 18, 4171-4174.
21. For a mild transesterification method, see: Mori, K.; Tominaga, M.; Takigawa, T.; Matsui, M. Synthesis 1973, 790-791.