Development of Synthetic Procedure of Allylamines via Oxidative Cyclization on Nickel and Unique Nickel/Aluminum Transmetalation

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Aza-aluminacyclopentenes, which serve a useful precursor for γ-substituted allylamines, were catalytically prepared from novel Ni-mediated three-component cyclocondensation reaction of an alkyne, an imine, and AlMe3. In this reaction, azanickelacycle generated by the oxidative cyclization of an alkyne and an imine is a key intermediate. On the other hand, the use of Me_2AlOTf as an additive allowed the oxidative cyclization of an aldehyde and an alkyne with nickel(0) to give an oxanickelacyclopentene, treatment of which with AlMe_3 yielded the corresponding oxaaluminacyclopentene.