Stereo- and regioselective synthesis of β-amino-β-tetrazolylvinylphosphonates

Addition of 5-substituted tetrazoles to dimethyl [(N,N-diisopropylamino)ethynyl]phosphonate proceeds regio- and stereoselectively to yield (Z)-[2-diisopropylamino-2-(tetrazolyl)vinyl]phosphonic acid dimethyl esters. The Z-configuration of the products was confirmed by 1Н NMR spectroscopy and single-crystal X-ray diffraction. The reactions occur via nucleophilic attack of tetrazole involving predominantly the N-1 atom of the tetrazole ring.