3-azabicyclo[3.1.0]hexane

3-Azabicyclo[3.1.0]hexane is a key structural feature found in a wide range of biologically active natural products, drugs, and agrochemicals.

3-azabicyclo[3.1.0]hexane synthesis: 1-Chlorocyclopropyl p-tolyl sulfoxides with an N,N-disubstituted aminomethyl group on the cyclopropane ring were prepared from dichloromethyl p-tolyl sulfoxide, α,β-unsaturated carboxylic acid esters, primary amines, and alkyl halides. Treatment of the sulfoxides with i-PrMgCl generated cyclopropylmagnesium carbenoids, which were inserted into an intramolecular C–H bond adjacent to a nitrogen atom to give 3-azabicyclo[3.1.0]hexane in yields of up to 94%.