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Stereocontrolled [ 11 C]Alkylation of N‐Terminal Glycine Schiff Bases To Obtain Dipeptides
Author(s) -
Filp Ulrike,
Pekošak Aleksandra,
Poot Alex J.,
Windhorst Albert D.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701129
Subject(s) - chemistry , alkylation , diastereomer , halide , methyl iodide , iodide , alkyl , catalysis , stereoselectivity , ethyl iodide , glycine , enantioselective synthesis , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , amino acid , biochemistry
The use of various quaternary ammonium salts as chiral phase‐transfer catalysts allowed effective and stereoselective radiochemical [ 11 C]alkylation to obtain functionalized dipeptides. We herein report a broadly applicable procedure for the asymmetric [ 11 C]alkylation of dipeptides to give labeled N‐terminal peptides by using different [ 11 C]alkyl halides. Contended stereoselectivities of the reactions were observed by using 11 C‐labeled alkyl halides, [ 11 C]methyl iodide and [ 11 C]benzyl iodide, and diastereomeric ratios with different specialized catalysts of 95:5 and 90:10 were achieved, respectively. Accordingly, the straightforward synthesis of enantioenriched compounds should play a vital role in peptide‐based radiopharmaceutical development and positron emission tomography imaging.