Reaction of Magnesium Cyclopropylidene with N-Lithio Arylamines: A Method for Generation of α-Amino-Substituted Cyclopropylmagnesiums and a Study for Their Reactivity with Electrophiles.

Abstract Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at −78 °C in high yield by a sulfoxide–magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give α-amino-substituted cyclopropylmagnesiums. The reaction of the α-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized.