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Issue 36, 2013
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C–C bond fragmentation by Grob/Eschenmoser reactions, applications in dendrimer synthesis

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Abstract

C–C bond fragmentation of structurally diverse carbocycles has been applied to the divergent synthesis of dendrimers. The fragmentation has been paired to deprotection or thio-Michael reaction, allowing the preparation of a fourth generation dendrimer of narrow molecular weight distribution. Methodologies to increase water solubility have been examined using appended carboxylic acid or oligoether moieties. In addition, incorporation of chiral prolinol derivatives has resulted in the synthesis of dendrimers that have been shown to catalyse the α-amination of aldehydes in good yield and modest enantioselectivity.

Graphical abstract: C–C bond fragmentation by Grob/Eschenmoser reactions, applications in dendrimer synthesis

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Supplementary files

Article information


Submitted
22 Apr 2013
Accepted
26 Jul 2013
First published
30 Jul 2013

Org. Biomol. Chem., 2013,11, 6150-6160
Article type
Paper

C–C bond fragmentation by Grob/Eschenmoser reactions, applications in dendrimer synthesis

J. Hierold and D. W. Lupton, Org. Biomol. Chem., 2013, 11, 6150
DOI: 10.1039/C3OB40800K

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