Synthesis of aromatic amine phosphonato ester derivatives from the stereoselective reaction between triphenyl phosphite and dimethyl acetylenedicarboxylate in the presence of derivatives of aromatic amines

Aromatic amine phosphonato esters 4a–d were obtained in excellent yields from the 1:1:1 addition reaction between triphenyl phosphite and dimethyl acetylenedicarboxylate in the presence of NH‐aromatic amines such as 2‐aminobenzophenone, 2‐aminoacetophenon, methyl‐2‐aminobenzoate, and 2‐aminobenzonitrile. In the recent works, the assignments of the configuration of 4a–d corresponding to the three‐bond carbon‐phosphorus coupling, ³Jpc, was determined on the basis of coupling constants by the Karplus equation as 2R *, 3R *or 2S *, 3S * while they were 2R *, 3S * or 2S *, 3R * in our previous works in the presence of same solvent. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:240–245, 2009; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20541