Synthesis of Enantiomerically Pure (α‐Phenylalkyl)amines with Substituents at the <i>ortho</i> Position through Diastereoselective Radical Alkylation Reaction of Sulfinimines

Abstract

Abstract The alkyl radical (R 1 ) addition reaction to ortho ‐X‐substituted N ‐(benzylidene)‐2‐methylpropane‐2‐sulfinamides (X = Br, CN, CO 2 Me, OH and OMe) is highly diastereoselective, regardless of the electronic properties of the X group and the size of R 1 . Easy removal of the sulfinyl group provides the title compounds in enantiomerically pure form. This two‐step sequence has been successfully applied to the preparation of primary α‐( tert ‐butyl)‐ ortho ‐hydroxy‐ and ‐ ortho ‐methoxybenzylamines, as well as the 3‐isopropyl‐substituted isoindolin‐1‐one.