Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols
Ruirui Xu, Kun Wang, Haoying Liu, Weijun Tang, Huaming Sun, Dong Xue, Jianliang Xiao, Chao Wang
Abstract
Abstract A ruthenium‐catalyzed formal anti‐Markovnikov hydroamination of allylic alcohols for the synthesis of chiral γ‐amino alcohols is presented. Proceeding via an asymmetric hydrogen‐borrowing process, the catalysis allows racemic secondary allylic alcohols to react with various amines, affording enantiomerically enriched chiral γ‐amino alcohols with broad substrate scope and excellent enantioselectivities (68 examples, up to >99 % ee ).
Topics & Concepts
Markovnikov's ruleHydroaminationAllylic rearrangementChemistryCatalysisOrganic chemistryEnantioselective synthesisRutheniumAlcoholCombinatorial chemistryRegioselectivityAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisCarbon dioxide utilization in catalysis