Iterative direct C(sp3)–H functionalization of amines: diastereoselective divergent syntheses of α,α′-disubstituted alicyclic amines

A novel iterative C(sp3)-H oxygenation/C-C bond formation strategy, which avoids repetitive N-protection/-deprotection steps, was developed for direct α,α'-difunctionalization of alicyclic amines. The method is highly efficient and stereoselective in producing syn-α,α'-disubstituted aliphatic N-heterocycles. Synthetic potential and practicability of the method was demonstrated by an easy and straightforward synthesis of neuroactive alkaloid nor-lobelane and its derivatives.