Chiral objects with a dendritic architecture

Chirality

Volumn 10, Issue 1-2, 1998, Pages 46-52

  Peerlings, H W I ^a   Struijk, M P ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Accidental degeneracy; Circular dichroism; Cryptochirality; Dendrimers; Dendritic wedges; Solketal

Indexed keywords

DENDRIMER; GLYCEROL; PROPANE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0031931652     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.9     Document Type: Article

References (31)

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19. Seebach, D., Lapierre, J.-M., Greiveldinger, G., Skobridis, K. Chirale tris(hydroxymethyl)methan-derivate als Synthesebausteine für chirale Dendrimere. Angew. Chem. 106:457-458, 1994; Seebach, D., Lapierre, J.-M., Greiveldinger, G., Skobridis, K. Synthesis of chiral starburst dendrimers from PHB-derived triols as central cores, Helv. Chim. Acta 77:1673-1688, 1994; Twyman, L.J., Beezer, A.E., Mitchell, J.C. The synthesis of chiral dendritic molecules based on the repeat unit L-glutamic acid. Tetrahedron Lett. 35:4423-4424, 1994; McElhanon, J., Wu, M.-J., Escobar, M., McGrath, D.V. The synthesis of optically active chiral dendrimers with 1,2-diol linkages. Polymer Preprints, 1996.
20. Seebach, D., Lapierre, J.-M., Greiveldinger, G., Skobridis, K. Chirale tris(hydroxymethyl)methan-derivate als Synthesebausteine für chirale Dendrimere. Angew. Chem. 106:457-458, 1994; Seebach, D., Lapierre, J.-M., Greiveldinger, G., Skobridis, K. Synthesis of chiral starburst dendrimers from PHB-derived triols as central cores, Helv. Chim. Acta 77:1673-1688, 1994; Twyman, L.J., Beezer, A.E., Mitchell, J.C. The synthesis of chiral dendritic molecules based on the repeat unit L-glutamic acid. Tetrahedron Lett. 35:4423-4424, 1994; McElhanon, J., Wu, M.-J., Escobar, M., McGrath, D.V. The synthesis of optically active chiral dendrimers with 1,2-diol linkages. Polymer Preprints, 1996.
21. Chow, H.-F., Mak, C.C. Synthesis and structure-optical rotation relationships of homochiral, monodisperse, tartaric acid-based dendrimers. J. Chem. Soc. Perkin Trans. 1:2223-2228, 1994; Chang, H.-T., Chen, C.-T., Kondo, T., Siuzdak, G., Sharpless, K.B. Asymmetric dihydroxylation enables rapid construction of chiral dendrimers based on 1,2-diols. Angew. Chem. Int. Ed. Engl. 35:182-186, 1996; Mak, C.C., Chow, H.-F. Synthesis and chiroptical properties of optically active layer-block dendrimers. Chem. Commun. 1185-1186, 1996.
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23. Chow, H.-F., Mak, C.C. Synthesis and structure-optical rotation relationships of homochiral, monodisperse, tartaric acid-based dendrimers. J. Chem. Soc. Perkin Trans. 1:2223-2228, 1994; Chang, H.-T., Chen, C.-T., Kondo, T., Siuzdak, G., Sharpless, K.B. Asymmetric dihydroxylation enables rapid construction of chiral dendrimers based on 1,2-diols. Angew. Chem. Int. Ed. Engl. 35:182-186, 1996; Mak, C.C., Chow, H.-F. Synthesis and chiroptical properties of optically active layer-block dendrimers. Chem. Commun. 1185-1186, 1996.
24. Murer, P., Seebach, D. Synthese und Eigenschaften von Dendrimeren Erster bis Dritter Generation mit zwei- und dreifach verzweigenden chiralen Bausteinen. Angew. Chem. 107:2297-2300, 1995.
25. Jansen, J.F.G.A., Peerlings, H.W.I., de Brabander-Van den Berg, E.M.M., Meijer, E.W. Optische Aktivität chiraler dendritischer Oberflächen. Angew. Chem. 107:1321-1324, 1995; Peerlings, H.W.I., Jansen, J.F.G.A., de Brabander-Van den Berg, E.M.M., Meijer, E.W. Optical activity of dendrimers with chiral end groups. ACS, Polym. Sci. Eng. 73:342-343, 1995 ; Peerlings, H.W.I., Chirality in dendritic architecture. Chem. Eur. J. 3:1563-1570, 1997.
26. Jansen, J.F.G.A., Peerlings, H.W.I., de Brabander-Van den Berg, E.M.M., Meijer, E.W. Optische Aktivität chiraler dendritischer Oberflächen. Angew. Chem. 107:1321-1324, 1995; Peerlings, H.W.I., Jansen, J.F.G.A., de Brabander-Van den Berg, E.M.M., Meijer, E.W. Optical activity of dendrimers with chiral end groups. ACS, Polym. Sci. Eng. 73:342-343, 1995 ; Peerlings, H.W.I., Chirality in dendritic architecture. Chem. Eur. J. 3:1563-1570, 1997.
27. Jansen, J.F.G.A., Peerlings, H.W.I., de Brabander-Van den Berg, E.M.M., Meijer, E.W. Optische Aktivität chiraler dendritischer Oberflächen. Angew. Chem. 107:1321-1324, 1995; Peerlings, H.W.I., Jansen, J.F.G.A., de Brabander-Van den Berg, E.M.M., Meijer, E.W. Optical activity of dendrimers with chiral end groups. ACS, Polym. Sci. Eng. 73:342-343, 1995 ; Peerlings, H.W.I., Chirality in dendritic architecture. Chem. Eur. J. 3:1563-1570, 1997.
28. Kremers, J.A., Meijer, E.W. Synthesis and characterization of a chiral dendrimer derived from pentaerythritol. J. Org. Chem. 59:4262-4266, 1994; Kremers, J.A., Meijer, E.W. Chiral dendrimers derived from pentaerythritol. React. Funct. Polymers 26:137-144, 1995.
29. Kremers, J.A., Meijer, E.W. Synthesis and characterization of a chiral dendrimer derived from pentaerythritol. J. Org. Chem. 59:4262-4266, 1994; Kremers, J.A., Meijer, E.W. Chiral dendrimers derived from pentaerythritol. React. Funct. Polymers 26:137-144, 1995.
30. Hawker, C.J., Fréchet, J.M.J. Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules. J. Am. Chem. Soc. 112:7638-7647, 1990.
31. The use of the term cryptochirality is very controversial, as is experienced by the authors at the 1996 Bürgenstock conference on stereochemistry. See Hunziker, J. Conference Report. Euchem Stereochemistry Conference. Chimia 50:282-284, 1996.