2-IMINOXETANES FROM KETENIMINE-ALDEHYDE CYCLOADDITIONS. PART 1: SYNTHESIS AND CONTROLLED RING OPENING OF 2-N-p-TOLYLIMINO-3,3-DIMETHYL-4-PHENYLOXETANE

Article abstract of DOI:10.1016/S0040-4039(00)96266-X

Regiospecific cycloaddition of benzaldehyde to dimethylketene - N-p-tolylimine, catalyzed by lanthanide shift reagents, afforded the corresponding 2-iminoxetane.Controlled ring opening showed the oxetane to be a versatile building block for the synthesis of the corresponding acyclic -aminoalcohol, β-keto and β-hydroxyamide.In addition isomerization produced the corresponding 2-azetidinone (β-lactam).