Diastereocontrolled addition of organometallic reagents to S-chiral N-(tert-butanesulfinyl)-α-fluoroenimines

Tetrahedron Letters

Volumn 50, Issue 3, 2009, Pages 264-266

  Pierry, Camille ^a   Zoute, Ludivine ^a   Jubault, Philippe ^a   Pfund, Emmanuel ^b   Lequeux, Thierry ^b   Cahard, Dominique ^a   Couve Bonnaire, Samuel ^a   Pannecoucke, Xavier ^a  

^a Institut de Recherche en Chimie Organique Fine   (France)

^b Institut Des Sciences De La Matière Et Du Rayonnement   (France)

Author keywords

Diastereoselective synthesis; Enimines; Fluorine compounds; Grignard; Peptides mimics

Indexed keywords

ALLYLAMINE DERIVATIVE; FLUORINE DERIVATIVE; GRIGNARD REAGENT; N (TERT BUTANESULFINYL) ALPHA FLUOROENIMINE; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; OLEFINATION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 57149128060     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.10.140     Document Type: Article

References (30)

1. In: Kirsch P. (Ed). Modern Fluoroorganic Chemistry (2004), Wiley-VCH, Weinheim
2. In: Chambers R.D. (Ed). Fluorine in Organic Chemistry (2004), Blackwell, Oxford
3. Bégué, J.-P.; Bonnet-Delpon, D., Eds.; Chimie bioorganique et médicinale du fluor; CNRS Editions: Paris, 2005 or Bioorganic and Medicinal Chemistry of Fluorine; John Wiley & Sons, Inc., 2008.
4. Thayer A. Chem. Eng. News 84 (2006) 15-24
5. Purser S., Moore P.R., Swallow S., and Gouverneur V. Chem. Soc. Rev. 37 (2008) 320-330
6. Hagmann W.K. J. Med. Chem. 51 (2008) 4359-4369
7. Shah P., and Westwell A.D. J. Enzyme Inhib. Med. Chem. 22 (2007) 527-540
8. Kirk K.L. J. Fluorine Chem. 127 (2006) 1013-1029
9. Special issue of. J. Fluorine Chem. 129 (2008) 725-888
10. Couve-Bonnaire S., Cahard D., and Pannecoucke X. Org. Biomol. Chem. 5 (2007) 1151-1157
11. Welch J.T., Lin J., Boros L.G., DeCorte B., Bergmann K., and Gimi R. In: Ojima I., McCarthy J.R., and Welch J.T. (Eds). Biomedical Frontiers of Fluorine Chemistry (1996), ACS Symp. Ser., Washington, DC 129-142
12. Edmondson S.D., Wei L., Xu J., Shang J., Xu S., Pang J., Chaudhary A., Dean D.C., He H., Leiting B., Lyons K.A., Patel R.A., Patel S.B., Scapin G., Wu J.K., Beconi M.G., Thornberry N.A., and Weber A.E. Bioorg. Med. Chem. Lett. 18 (2008) 2409-2413
13. Van der Veken P., Senten K., Kertesz I., De Meester I., Lambeir A.-M., Maes M.-B., Scharpé S., Haemers A., and Augustyns K. J. Med. Chem. 48 (2005) 1768-1780
14. Van der Veken P., Kertesz I., Senten K., Haemers A., and Augustyns K. Tetrahedron Lett. 44 (2003) 6231-6234
15. Lin J., Toscano P.J., and Welch J.T. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 14020-14024
16. Zhao K., Lim D.S., Funaki T., and Welch J.T. Bioorg. Med. Chem. 11 (2003) 207-215
17. Welch J.T., and Lin J. Tetrahedron 52 (1996) 291-304
18. Allmendinger T., Felder E., and Hungerbühler E. Tetrahedron Lett. 31 (1990) 7301-7304
19. Waelchli R., Gamse R., Bauer W., Meigel H., Lier E., and Feyen J.H.M. Bioorg. Med. Chem. Lett. 6 (1996) 1151-1156
20. Lamy C., Hofmann J., Parrot-Lopez H., and Goekjian P. Tetrahedron Lett. 48 (2007) 6177-6180
21. Narumi T., Tomita K., Inokuchi E., Kobayashi K., Oishi S., Ohno H., and Fujii N. Tetrahedron 64 (2008) 4332-4346
22. Tomita K., Narumi T., Niida A., Oishi S., Ohno H., and Fujii N. Biopolymers 88 (2007) 272-278
23. Dutheuil G., Couve-Bonnaire S., and Pannecoucke X. Angew. Chem., Int. Ed. 46 (2007) 1290-1292
24. Dutheuil G., Bailly L., Couve Bonnaire S., and Pannecoucke X. J. Fluorine Chem. 128 (2007) 34-39
25. For examples of addition of organometallics to chiral sulfinimides see:. Ellman J.A., Owens T.D., and Tang T.P. Acc. Chem. Res. 35 (2002) 984-995
26. Morton D., and Storkman R.A. Tetrahedron 62 (2006) 8869-8905
27. Zoute, L. Ph.D. Thesis, INSA of Rouen, 2007.
28. Lemonnier, G. Ph.D. Thesis, INSA of Rouen, 2008.
29. Pfund E., Lebargy C., Rouden J., and Lequeux T. J. Org. Chem. 72 (2007) 7871-7877
30. 2SSi: C, 67.02; H, 8.04; N, 2.79. Found: C, 67.25; H, 8.11; N, 2.77.