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Synthesis of aromatic bis- and tris(amino acids) and chiral dendrimers

Ritzén, Andreas LU (1999)
Abstract
A number of protected aromatic bis- and tris(amino acids) have been synthesised by catalytic asymmetric hydrogenation of the corresponding didehydroamino acid derivatives. The didehydroamino acid derivatives were prepared either by a Heck coupling of a 2-amidoacrylate with an aryl dihalide, or by Horner-Wadsworth-Emmons olefination of aromatic aldehydes with phosphonylglycine reagents. Excellent stereochemical purity could be achieved in most cases.



The bis- and tris(amino acids) were then used as building blocks in a model study, the purpose of which was to assess the feasibility of constructing synthetic receptors from tris(amino acids). Several macrocyclic peptide-like compounds were prepared.



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A number of protected aromatic bis- and tris(amino acids) have been synthesised by catalytic asymmetric hydrogenation of the corresponding didehydroamino acid derivatives. The didehydroamino acid derivatives were prepared either by a Heck coupling of a 2-amidoacrylate with an aryl dihalide, or by Horner-Wadsworth-Emmons olefination of aromatic aldehydes with phosphonylglycine reagents. Excellent stereochemical purity could be achieved in most cases.



The bis- and tris(amino acids) were then used as building blocks in a model study, the purpose of which was to assess the feasibility of constructing synthetic receptors from tris(amino acids). Several macrocyclic peptide-like compounds were prepared.



Chiral dendrimers were also synthesised from the bis- and tris(amino acids). These dendrimers could be deprotected to yield water-soluble, polycationic or polyanionic macromolecules with a common structure. A chiroptical study of the protected dendrimers was undertaken, and it indicated that the solution shape is rather flat and sterically uncongested. (Less)
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author
opponent
  • Prof Liskamp, Rob. M. J., Utrecht University, The Netherlands
organization
publishing date
type
Thesis
publication status
published
subject
keywords
Organisk kemi, Organic chemistry, HWE reaction, asymmetric hydrogenation, Heck reaction, Amino acids, chiral dendrimers
pages
66 pages
publisher
Department of Organic Chemistry, Lund University
defense location
Center for Chemistry and Chemical Engineering
defense date
2000-01-21 10:15
external identifiers
  • Other:ISRN: LUNDL/NKOK-1041-SE
language
English
LU publication?
yes
id
8a6606c5-758f-4a9e-a6ec-b6ecde73d8b4 (old id 40186)
date added to LUP
2007-10-14 17:20:14
date last changed
2016-09-19 08:45:09
@misc{8a6606c5-758f-4a9e-a6ec-b6ecde73d8b4,
  abstract     = {A number of protected aromatic bis- and tris(amino acids) have been synthesised by catalytic asymmetric hydrogenation of the corresponding didehydroamino acid derivatives. The didehydroamino acid derivatives were prepared either by a Heck coupling of a 2-amidoacrylate with an aryl dihalide, or by Horner-Wadsworth-Emmons olefination of aromatic aldehydes with phosphonylglycine reagents. Excellent stereochemical purity could be achieved in most cases.<br/><br>
<br/><br>
The bis- and tris(amino acids) were then used as building blocks in a model study, the purpose of which was to assess the feasibility of constructing synthetic receptors from tris(amino acids). Several macrocyclic peptide-like compounds were prepared.<br/><br>
<br/><br>
Chiral dendrimers were also synthesised from the bis- and tris(amino acids). These dendrimers could be deprotected to yield water-soluble, polycationic or polyanionic macromolecules with a common structure. A chiroptical study of the protected dendrimers was undertaken, and it indicated that the solution shape is rather flat and sterically uncongested.},
  author       = {Ritzén, Andreas},
  keyword      = {Organisk kemi,Organic chemistry,HWE reaction,asymmetric hydrogenation,Heck reaction,Amino acids,chiral dendrimers},
  language     = {eng},
  pages        = {66},
  publisher    = {ARRAY(0x86e0090)},
  title        = {Synthesis of aromatic bis- and tris(amino acids) and chiral dendrimers},
  year         = {1999},
}