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Development of new precursors for asymmetric preparation of alpha-[11C] methyl amino acids for PET

18 June 2008

PhD ceremony: A. Popkov, 16.15 uur, Academiegebouw, Broerstraat 5, Groningen

Thesis: Development of new precursors for asymmetric preparation of alpha-[11C] methyl amino acids for PET

Promotor(s): prof. R.A. Dierckx, prof. P.H. Elsinga, prof. A. Lycka (Tjechië)

Faculty: Medical Sciences

 

The main aims of the work presented in this thesis are: 1. to increase stereochemical output of alkylation of the chiral nickel complexes derived from amino acids in order to avoid or at least simplify separation of diastereomeric products of alkylation; 2. to develop a new approach to creation of quaternary asymmetric centre via alkylation of a chiral tertiary carbanion by 11CH3I or 11CH3OTfand evaluate the applicability of metallocomplex chiral synthons of a -amino acids for asymmetric synthesis of 11C-labeled a -methyl amino acids.Proximity of ortho-protons of the benzyl group to both the a -proton of the proline residue and substituents in a -position of the amino acid fragment in CDCl3 solution of the simplest studied complex led to formulation of the first hypothesis about structure of the improved synthon providing higher asymmetric induction. It should carry substituents in ortho-positions of the benzyl group.

In the same complex the polarisation of electron density in an aromatic electron cloud of the benzyl group towards positively charged nickel atoms is proved by experiment.Introduction of -C(CH3)3 substituents in meta-positions of the benzyl group or use the pentamethylbenzyl group in Ni(II) complexes of Schiff bases of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and glycine and alanine gave very efficient synthons of glycine and alanine capable of stereospecific preparation of a -monosubstituted glycines or highly stereoselective synthesis of a -methyl a -amino acids.

Last modified:15 September 2017 3.38 p.m.
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