261518-58-5Relevant articles and documents
Synthesis of [18 F]-γ-Fluoro-α,β-unsaturated Esters and Ketones via Vinylogous 18 F-Fluorination of α-Diazoacetates with [18 F]AgF
Brooks, Allen F.,Ichiishi, Naoko,Jackson, Isaac M.,Lee, So Jeong,Sanford, Melanie S.,Scott, Peter J. H.,Thompson, Stephen
, p. 4401 - 4407 (2019)
This communication reports a method for the vinylogous radiofluorination of α-diazoacetates to generate [18 F]-γ-fluoro-α,β-unsaturated esters and ketones in moderate to good radiochemical yields. The method uses no-carrier-added [18 F]AgF and is compatible with aromatic and non-aromatic substrates and a number of different functional groups. The labeling method is showcased in the synthesis of a fluorinated cholest-5-en-3-one derivative as well as a difluorinated product pertinent to drug discovery.
Synthesis of γ-Fluoro-α,β-unsaturated Carboxylic Esters from Saturated α-Fluoro Aldehydes
Oldendorf, Jens,Haufe, Gu?nter
, p. 52 - 57 (2007/10/03)
γ-Fluoro-α,β-unsaturated carboxylic esters 7a, 7b and 7d and 4-fluoro-4-phenylbut-3-enoic ester (8) are obtained by two alternative pathways from 2-fluoro aldehydes 5a-d, either by Horner-Wadsworth-Emmons reaction or by Wittig reaction. The aldehydes 5a-d are prepared by Swern oxidation of the corresponding fluorohydrins 4a-d. These are available from α-olefins by bromofluorination, bromine-by-acetate replacement and subsequent hydrolysis.
