A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

• Natalia V. Pavlenko,
• Tatiana I. Oos,
• Yurii L. Yagupolskii,
• Igor I. Gerus,
• Uwe Doeller and
• Lothar Willms

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