Beilstein J. Org. Chem.2014,10, 722–731, doi:10.3762/bjoc.10.66
, alanine, valine, proline, aminomalonic and aspartic acids were thus prepared. Three-component one-pot reactions of (trifluoromethyl)phosphinic acid and dibenzylamine with aldehydes were also tested to prepare the title compounds.
Keywords: (1-aminoalkyl)phosphinic acids; ethyl (difluoromethyl)phosphinate
(trifluoromethyl)- or (difluoromethyl)phosphonyl moiety instead of the carboxylate function. To the best of our knowledge there is only one report on the application of ethyl (difluoromethyl)phosphinate CHF2(H)P(O)(OEt) in the synthesis of a (difluoromethyl)phosphinic acid analogue of GABA, as a potent agonist of
when freshly prepared and distilled.
We next explored the CHF2 group attached to phosphorus. Ethyl (difluoromethyl)phosphinate CHF2P(O)H(OEt) (5) was prepared as previously described [18]. The appropriate (difluoromethyl)phosphinic acid CHF2P(O)H(OH) (6) was obtained from 5 by ester deprotection with
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Graphical Abstract
Scheme 1:
Synthesis of (trifluoromethyl)phosphinic acid (1) and ethyl and isopropyl esters 2–4. Reagents and ...