Novel syntheses by directed lithiations of N-Boc benzylamines and cyclopropylamines

The lithiation-substitution of N-Boc benzylamines and cyclopropylamines have been investigated to explore the synthetic potential of these substrates. We have achieved the syntheses of highly enantioenriched benzylic $\alpha$-substituted N-Boc secondary amines using RLi/(-)-sparteine. Extension of this chemistry to asymmetric syntheses of both enantiomers of primary $\alpha$-substituted benzylamines and $\alpha,\alpha$-disubstituted benzylamines has been achieved successfully. Also, the N-Boc group was used as an activating and directing group for the $\alpha$ and $\beta$ lithiation-substitution of cyclopropanes. Extension of this chemistry to syntheses of highly functionalized cyclopentane by (3 + 2) cycloaddition and asymmetric synthesis of N-Boc azabicyclic (3.10) hexane was investigated.U of I OnlyETDs are only available to UIUC Users without author permissio