Functionalised, chiral imidazolium compounds from proteinogenic amino acids

• Authors: Olaf Kühl , Stephan Millinghaus , Philipp Wehage
• Languages of publication: EN

Abstracts

EN

Chiral, carboxylic acid-functionalised imidazolium zwitterions were synthesised from the corresponding L-amino acids leucine, valine and isoleucine.

Keywords

EN

Amino acids; Imidazolium; Chirality; Zwitterion; Functionalised carbenes

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 6
• Pages: 1223-1226

Dates

published

1 - 12 - 2010

online

8 - 10 - 2010

Contributors

author

Olaf Kühl

• Bioinorganic Research Group, Institute for Biochemistry, Ernst-Moritz-Arndt-University Greifswald, Felix-Hausdorff-Str. 4, D-17489, Greifswald, Germany

author

Stephan Millinghaus

• Bioinorganic Research Group, Institute for Biochemistry, Ernst-Moritz-Arndt-University Greifswald, Felix-Hausdorff-Str. 4, D-17489, Greifswald, Germany

author

Philipp Wehage

• Bioinorganic Research Group, Institute for Biochemistry, Ernst-Moritz-Arndt-University Greifswald, Felix-Hausdorff-Str. 4, D-17489, Greifswald, Germany

References

• [1] F. Glorius, N-Heterocyclic Carbenes in Transition Metal Catalysis (Springer-Verlag, Heidelberg, 2006)
• [2] R.R. Schrock, Angew. Chem. 118, 3832 (2006) http://dx.doi.org/10.1002/ange.200600085[Crossref]
• [3] K. Öfele, J. Organomet. Chem. 12, 42 (1968) http://dx.doi.org/10.1016/S0022-328X(00)88691-X[Crossref]
• [4] H.-W. Wanzlick, H.-J. Schönherr, Angew. Chem. 80, 154 (1968) http://dx.doi.org/10.1002/ange.19680800411[Crossref]
• [5] A.J. Arduengo III, R.L. Harlow, M. Kline, J. Am. Chem. Soc. 113, 361 (1991) http://dx.doi.org/10.1021/ja00001a054[Crossref]
• [6] H.M.J. Wang, I.J.B. Lin, Organometallics 17, 972 (1998) http://dx.doi.org/10.1021/om9709704[Crossref]
• [7] M.C. Perry, K. Burgess, Tetrahedron: Asymmetry 14, 951 (2003) http://dx.doi.org/10.1016/S0957-4166(03)00037-5[Crossref]
• [8] V. César, S. Bellemin-Laponnaz, L.H. Gade, Chem. Soc. Rev. 33, 619 (2004) http://dx.doi.org/10.1039/b406802p[Crossref]
• [9] T. Focken, G. Raabe, C. Bolm, Tetrahedron: Asymmetry 15, 1693 (2004) http://dx.doi.org/10.1016/j.tetasy.2004.03.047[Crossref]
• [10] S. Gischig, A. Togni, Organometallics 24, 203 (2005) http://dx.doi.org/10.1021/om049097e[Crossref]
• [11] L.P. Spencer, S. Winston, M. D. Fryzuk, Organometallics 23, 3372 (2004) http://dx.doi.org/10.1021/om0498089[Crossref]
• [12] S.A. Mungur, S.T. Liddle, C. Wilson, M.J. Sarsfield, P.L. Arnold, Chem. Comm. 2738 (2004) [Crossref]
• [13] P.L. Arnold, A.C. Scarisbrick, A.J. Blake, C. Wilson, Chem. Comm. 2340 (2001) [Crossref]
• [14] J.J. Van Veldhuizen, S.B. Garber, J.S. Kingsbury, A.H. Hoveyda, J. Am. Chem. Soc. 124, 4954 (2002) http://dx.doi.org/10.1021/ja020259c[Crossref]
• [15] O. Kühl, Functionalised N-Heterocyclic Carbene Complexes (Wiley & Sons, Chichester, 2010) http://dx.doi.org/10.1002/9780470685839[Crossref]
• [16] O. Kühl, Chem. Soc. Rev. 36, 592 (2007) http://dx.doi.org/10.1039/b603765h[Crossref]
• [17] S. Shanmuganathan, O. Kühl, P.G. Jones, J. Heinicke, Cent. Eur. J. Chem. 8, 992 (2010) http://dx.doi.org/10.2478/s11532-010-0071-6[Crossref]
• [18] L. Ray, V. Katiyar, M.J. Raihan, H. Nanavati, M.M. Shaikh, P. Ghosh, Eur. J. Inorg. Chem. 3724 (2006)
• [19] J.J. Velisek, Food Sci. 54, 1544 (1989) http://dx.doi.org/10.1111/j.1365-2621.1989.tb05155.x[Crossref]
• [20] O. Kühl, S. Shanmuganathan, F. Ullah, M.K. Kindermann, P.G. Jones, M. Köckerling, J. Heinicke, Polyhedron 27, 2825 (2008) http://dx.doi.org/10.1016/j.poly.2008.06.006[Crossref]
• [21] O. Kühl, K. Lifson, W. Langel, Eur. J. Org. Chem. 2336 (2006) [Crossref]
• [22] F. Grisi, C. Costabile, E. Gallo, A. Mariconda, C. Tedesco, P. Longo, Organometallics 27, 4649 (2008) http://dx.doi.org/10.1021/om800459y[Crossref]
• [23] H. Clavier, L. Boulanger, N. Audic, L. Toupet, M. Mauduit, J.-C. Guillemin, Chem. Comm. 1224 (2004) [Crossref]
• [24] B. Altava, D.S. Barbosa, M.I. Burguete, J. Escorihuela, S.V. Luis, Tetrahedron: Asymmetry 20, 999 (2009) http://dx.doi.org/10.1016/j.tetasy.2009.03.028[Crossref]
• [25] A. Meyer, M.A. Taige, T. Strasser, J. Organomet. Chem. 694, 1861 (2009) http://dx.doi.org/10.1016/j.jorganchem.2009.01.036[Crossref]
• [26] F. J.-B. Dit Dominique, H. Gornitzka, C. Hemmert, Organometallics 29, 2868 (2010) http://dx.doi.org/10.1021/om100048d[Crossref]
• [27] O. Kühl, G. J. Palm, Tetrahedron: Asymmetry 21, 393 (2010) http://dx.doi.org/10.1016/j.tetasy.2010.02.015[Crossref]
• [28] O. Kühl, P. Lönnecke, J. Heinicke, Polyhedron, 20, 2215 (2001) http://dx.doi.org/10.1016/S0277-5387(01)00821-X[Crossref]

Identifiers

DOI

10.2478/s11532-010-0097-9