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; Lothar Willms

doi:10.3762/bjoc.10.66

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

Beilstein J Org Chem. 2014 Mar 26:10:722-31. doi: 10.3762/bjoc.10.66. eCollection 2014.

Authors

Natalia V Pavlenko¹, Tatiana I Oos¹, Yurii L Yagupolskii¹, Igor I Gerus², Uwe Doeller³, Lothar Willms³

Affiliations

¹ Institute of Organic Chemistry National Academy of Sciences of Ukraine, Murmanskaya str. 5, 02660 Kiev-94, Ukraine.
² Institute of Bioorganic Chemistry and Petrochemistry National Academy of Sciences of Ukraine, Murmanskaya str. 1, 02660 Kiev-94, Ukraine.
³ Bayer CropScience Aktiengesellschaft BCS AG-R-WC-WCC-C2 Weed Control Chemistry 2, Frankfurt, G836, 101, Germany.

Abstract

A series of novel (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids - analogues of proteinogenic and nonproteinogenic α-amino acids were prepared. The synthetic methodology was based on nucleophilic addition of (trifluoromethyl)phosphinic acid 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)phosphinic acid and dibenzylamine with aldehydes were also tested to prepare the title compounds.

Keywords: (1-aminoalkyl)phosphinic acids; (trifluoromethyl)phosphinic acid; Shiff bases; ethyl (difluoromethyl)phosphinate; hydrophosphinylation; organo-fluorine.