Stereoselective reduction of N-(3-arylcyclobutylidene)amines

N-Alkylimines derived from cyclobutanones have not been evaluated in depth as building blocks for organic synthesis, although these compounds are, among others, good precursors for interesting 3-arylcyclobutylamines. The reduction of various N-alkyl-N-(3-arylcyclobutylidene)amines with LiAlH₄ yielded cis-substituted cyclobutylamines as the only stereoisomers. When borane was used as a reducing agent, an intermediate imine-borane complex could be isolated as a stable compound.