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

Beilstein Journal of Organic Chemistry

Lothar Willms¹  Uwe Doeller¹  Igor I. Gerus²  Natalia V. Pavlenko³  Tatiana I. Oos³  Yurii L. Yagupolskii³ 

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

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

DOI  :  10.3762/bjoc.10.66

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown