Exploitation of differential electronic densities for the stereoselective reduction of ketones bearing a masked amino surrogate

Abstract

A tethered ruthenium-TsDPEN catalyst is employed for the facile catalytic asymmetric reduction of α-phthalimyl-α′-ketoethers under mild conditions. Leveraging exclusively on the contrasting electronic densities on the heteroatoms, a series of enantioenriched phthalimyl ether alcohols can be obtained in generally good stereoselectivities from this challenging class of substrate. Subsequent transformation into highly valuable chiral β-amino alcohols is demonstrated to take place without significant losses in yield and optical purity.