beta-substituted propionamides (RCHXCR(1)R(2)CONHAr) were synthesized
in high yields by addition of protic and aprotic Lewis acids (C6H5SO3H
, CF3COOH, CH3COOH, HI, MgBr2, ZnI2, CH3OH, H2O,2,4,6-(NO2)(3)C6H2OH)
to 2-iminooxetanes. Studies on the stereochemistry of the acid additio
n to unsymmetrically C3,C4-monosubstituted 2-iminooxetanes indicate th
at product distribution depends on the steric and electronic nature of
the substitutents of the oxetane moiety as well as on the nucleophili
city of the conjugate base derived from the acid.