Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols

This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of alpha-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.

Automated summary

This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of alpha-iminoketones for accessing chiral vicinal amino alcohols. The methodology offers advantages such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields and stereoselectivities. Furthermore, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.