Beilstein J. Org. Chem.2014,10, 722–731, doi:10.3762/bjoc.10.66
proteinogenic and nonproteinogenic α-amino acids were prepared. The synthetic methodology was based on nucleophilic addition of (trifluoromethyl)phosphinicacid or (difluoromethyl)phosphinic acid or its ethyl ester to substrates with C=N or activated C=C double bonds. Analogues of glycine, phenylglycine
, alanine, valine, proline, aminomalonic and aspartic acids were thus prepared. Three-component one-pot reactions of (trifluoromethyl)phosphinicacid and dibenzylamine with aldehydes were also tested to prepare the title compounds.
Keywords: (1-aminoalkyl)phosphinic acids; ethyl (difluoromethyl)phosphinate
; hydrophosphinylation; organo-fluorine; Shiff bases; (trifluoromethyl)phosphinicacid; Introduction
For a long time aminophosphonic and aminophosphinic acids as isosters of aminocarboxylic acids have attracted a particular interest for the preparation of analogues of numerous natural products. Among the literature
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Graphical Abstract
Scheme 1:
Synthesis of (trifluoromethyl)phosphinic acid (1) and ethyl and isopropyl esters 2–4. Reagents and ...