Chemoselective Synthesis of δ-Amino Alcohols from Chiral 1,4-Diols Catalyzed by an NHC–Ir(III) Complex

The synthesis of δ-amino alcohols from 1,4-diols via the <i>hydrogen borrowing</i> strategy by an NHC-Ir(III) catalyst is described. The amination occurs on the primary alcohol selectively. The mild, base-free conditions effectively suppress the common second intramolecular amination to pyrrolidines. <i>sec</i>-Alcohols, even benzylic ones, remain inert toward amination and even without racemization, enabling the synthesis of chiral δ-amino alcohols from readily available chiral 1,4-diols. Late-stage functionalization (LSF) of Lenalidomide and other complex drugs is demonstrated.