Synthesis of a series of novel spiroisoxazolines has been accomplished in good yields by regio- and diastereoselective 1,3-dipolar cycloaddition of (E)-2-arylidene-(2H)-indanones 1a-d and (E)-2-arylidene-(2H)-3-methylindanones 2a-d to arylnitrile oxides 3e-g. The structure of the spiroadducts was elucidated by 1H and 13C NMR. The proposed regio- and stereochemistry of spiranic compounds 4ae-dg and 5ae-dg has been corroborated by two single crystal X-Ray diffraction studies.
S. Boudriga, N. Wannassi, M. Askri, M.E.B. Rammah, C. Strohmann
1,3-dipolar cycloaddition, regiochemistry, stereochemistry, spiroisoxazolines