Synthesis of fluorinated pseudopeptides: Metal mediated reversal of stereochemistry in diastereoselective addition of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines

Organic and Biomolecular Chemistry

Volumn 9, Issue 7, 2011, Pages 2378-2386

  Pierry, Camille ^a   Cahard, Dominique ^a   Couve Bonnaire, Samuel ^a   Pannecoucke, Xavier ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL AMINE; DIASTEREOMERIC RATIOS; DIASTEREOSELECTIVE ADDITIONS; GRIGNARD REAGENT; HIGH YIELD; ORGANOMETALLIC REAGENT; PEPTIDE BONDS; STEREOGENIC CENTERS; SYNTHONS;

ADDITION REACTIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

BUTANE; FLUORINE DERIVATIVE; IMINE; ORGANOMETALLIC COMPOUND; PEPTIDE; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BUTANES; FLUORINE COMPOUNDS; IMINES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PEPTIDES; STEREOISOMERISM; SULFUR COMPOUNDS;

EID: 79952741022     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00773k     Document Type: Article

References (20)

1. J.-P. Bégué and D. Bonnet-Delpon, in Bioorganic and Medicinal Chemistry of fluorine, Wiley, 2008
2. Fluorine and Health (ed.:, A. Tressaud, G. Haufe,), Elsevier, 2008
3. Fluorine in Medicinal Chemistry and Chemical Biology (Ed.:, I. Ojima,), Wiley-Blackwell, 2009
4. A. M. Thayer Chem. Eng. News 2006 84 15 33
5. Fluorinated surfaces oatings and Films (ed.:, D. G. Castner, D. W. Grainger,), ACS Symposium Series, 2001
6. Fluorinated Materials for Energy Conversion (ed.:, T. Nakajima, H. Groult,), Elsevier, 2005
7. Fluorine and the environment: Agrochemicals Archaelogy, Green Chemistry and water, Volume 2 (Ed.:, A. Tressaud,), Elsevier, 2006
8. S. Couve-Bonnaire D. Cahard X. Pannecoucke Org. Biomol. Chem. 2007 5 1151 1157
9. G. Dutheuil S. Couve-Bonnaire X. Pannecoucke Angew. Chem., Int. Ed. 2007 46 1290 1292
10. C. Pierry L. Zoute P. Jubault E. Pfund T. Lequeux D. Cahard S. Couve-Bonnaire X. Pannecoucke Tetrahedron Lett. 2009 50 264 266
11. G. Alvaro P. Pacioni D. Savoia Chem.-Eur. J. 1997 3 726 731
12. G. Alvaro G. Martelli D. Savoia J. Chem. Soc., Perkin Trans. 1 1998 775 783
13. R. Almansa D. Guijarro M. Yus Tetrahedron: Asymmetry 2008 19 603 606
14. R. Almansa D. Guijarro M. Yus Tetrahedron: Asymmetry 2008 19 2484 2491
15. R. Almansa D. Guijarro M. Yus Tetrahedron Lett. 2009 50 3198 3201
16. R. Almansa D. Guijarro M. Yus Tetrahedron Lett. 2009 50 4188 4190
17. L. Zoute G. Dutheuil J.-C. Quirion P. Jubault X. Pannecoucke Synthesis 2006 20 3409 3418
18. G. Lemonnier L. Zoute G. Dupas J.-C. Quirion P. Jubault J. Org. Chem. 2009 74 4124 4131
19. M. T. Robak M. A. Herbage J. A. Ellman Chem. Rev. 2010 110 3600 3740
20. M. Hatano S. Suzuki K. Ishihara J. Am. Chem. Soc. 2006 128 9998 9999