TBADT‐Mediated Photocatalytic Stereoselective Radical Alkylation of Chiral N‐Sulfinyl Imines: Towards Efficient Synthesis of Diverse Chiral Amines
Matteo Leone, Joseph P. Milton, Dorota Gryko, Luc Neuville, Géraldine Masson
Abstract
Herein we describe a sustainable and efficient photocatalytic method for the stereoselective radical alkylation of chiral sulfinyl imines. By employing readily available non-prefunctionalized radical precursors and the cost-effective TBADT as a direct HAT photocatalyst, we successfully obtain diverse chiral amines with high yields and excellent diastereoselectivity under mild conditions. This method provides an efficient approach for accessing a diverse array of medicinally relevant compounds, including both natural and synthetic α-amino acids, aryl ethyl amines, and other structural motifs commonly found in approved pharmaceuticals and natural product.
Topics & Concepts
StereoselectivityAlkylationPhotocatalysisCombinatorial chemistryChemistryNatural productChiral auxiliaryOrganic chemistryEnantioselective synthesisCatalysisSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods