Diastereoselective Intramolecular Spirocyclization via C(sp³)−H Bond Functionalization Towards the Synthesis of 2,7‐Diazaspiro[4.5]decane‐1,3‐diones

Abstract

The C(sp3)‐H functionalization via intramolecular hydride transfer initiated cascade annulation for the synthesis of spiro‐fused succinimide‐containing tetrahydroquinolines induced by iminium intermediates is described. A series of diastereoselective 2,7‐diazaspiro[4.5]decanes‐1,3‐diones were achieved using ortho‐amino‐benzylidene‐succinimide using Lewis acid catalysis. This scandium triflate Sc(OTf)3 catalysed, oxidant‐free protocol leads to the diastereoselective synthesis of a class of 2,7‐diazaspiro[4.5]decanes‐1,3‐diones derivatives with 48‐98% yield in a single step.