SYNTHESIS OF AZETIDIN-3-ONES BY HETEROCYCLIZATION OF α-CYCLOHEXYLAMINO-α',β'-EPOXY KETONES

Article abstract of DOI:10.1007/BF00475317

The stereospecific cyclization of 5-aryl-2-methyl-5-methoxy-4-cyclohexylamino-1,2-epoxypentan-3-one borofluorides on heating in acetone or in acetonitrile leads to 4-arylmethoxymethyl-2-hydroxymethyl-2-methyl-1-cyclohexylazetidin-3-ones.Certain chemical transformations of the latter have been studied.It was shown that, in contrast to the borofluoride complex, 2-methyl-5-methoxy-5-phenyl-4-cyclohexylamino-1,2-epoxypentan-3-one cyclizes into a mixture of diastereomeric 2-(cyclohexylamino)tetrahydrofuran-3-ones.