Functionalized carbosilane dendritic species as soluble supports in organic synthesis

Neldes J. Hovestad, Allan Ford, Johann T. B. H. Jastrzebski, Gerard Van Koten

Research output: Contribution to journalArticleAcademicpeer-review


A new methodology, which is compatible with the use of reactive organometallic reagents, has been developed for the use of carbosilane dendrimers as soluble supports in organic synthesis. Hydroxy-functionalized dendritic carbosilanes Si[CH2CH2CH2SiMe2(C6H4CH(R)OH)]4(G0-OH, R = H or (S)-Me) and Si[CH2CH2CH2Si[CH2CH2CH2SiMe2(C6H4CH(R)OH)]3]4(G1-OH, R = H or (S)-Me) were prepared and subsequently converted into the esters Si[CH2CH2CH2SiMe2(C6H4-CH(R)OC(O)CH2Ph)]4(R = H or (S)-Me) and Si[CH2CH2CH2Si[CH2CH2CH2SiMe2(C6H4CH(R)OC-(O)CH2C6H4R')]3]4(R = H and R' = H or R = (S)-Me and R' = H or R = H and R' = Br). As an example the latter compound was functionalized under Suzuki conditions. The functionalized carboxylic acid was obtained in high yield after cleavage from the dendritic support. Moreover, the ester functionalized dendrimers were converted to the corresponding zinc enolates followed by a condensation reaction with an imine to a β-lactam in excellent yield and purity. Furthermore, it was demonstrated that a small combinatorial library of β-lactams could be prepared starting from a carbosilane dendrimer functionalized with different ester moieties. These results show that carbosilane dendrimers can be applied as soluble substrate carriers for the generation of low molecular weight organic molecules. In combination with nanofiltration techniques, separation and recycling of the dendrimers can be realized.
Original languageEnglish
Pages (from-to)6338-6344
Number of pages7
JournalJournal of Organic Chemistry
Issue number20
Publication statusPublished - 6 Oct 2000


  • beta lactam
  • bromine
  • carboxylic acid
  • dendrimer
  • ester derivative
  • hydrogen
  • imine
  • organic compound
  • reagent
  • silane derivative
  • zinc
  • article
  • chemical modification
  • chemical reaction
  • molecular weight
  • organic chemistry
  • polymerization
  • reaction analysis
  • synthesis


Dive into the research topics of 'Functionalized carbosilane dendritic species as soluble supports in organic synthesis'. Together they form a unique fingerprint.

Cite this