Catalytic Diastereo‐ and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen
Hui‐Jie Pan, Yamei Lin, Taotao Gao, Kai Kiat Lau, Wei Feng, Bin‐Miao Yang, Yu Zhao
Abstract
We present herein an unprecedented diastereoconvergent synthesis of vicinal diamines from diols through an economical, redox-neutral process. Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1,2-diols (as a mixture of diastereomers) couple to forge two C-N bonds in an efficient and diastereoselective fashion. By identifying an effective chiral iridium/phosphoric acid co-catalyzed procedure, the first enantioconvergent double amination of racemic 1,2-diols has also been achieved, resulting in a practical access to highly valuable enantioenriched vicinal diamines.
Topics & Concepts
VicinalChemistryDiastereomerCatalysisReductive aminationRutheniumOrganic chemistryAminationLewis acids and basesCombinatorial chemistryAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisSurface Chemistry and Catalysis