Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols
Jiang Wang, Xin Lin, Pan‐Lin Shao, Jingyuan Song, Jialin Wen, Xumu Zhang
Abstract
This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of α-iminoketones for accessing chiral vicinal amino alcohols, which are privileged motifs in pharmaceuticals, agrochemicals, fine chemicals, chiral auxiliaries, organocatalysts, etc. Compared with existing methods, this methodology has the following advantages, such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields (90 to 96%) and stereoselectivities (up to >99:1 dr; >99.9% ee). In addition, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.
Topics & Concepts
Enantiopure drugVicinalAsymmetric hydrogenationCatalysisChemistryCombinatorial chemistryOrganic chemistryEnantioselective synthesisReaction conditionsAsymmetric Hydrogenation and CatalysisCatalysis for Biomass ConversionCatalysis and Hydrodesulfurization Studies