A facile chiral tethered ruthenium-TsDPEN system is applied to the 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 good stereoselectivities from this challenging class of substrate. The obtained alcohols can be readily transformed into highly valuable chiral β-amino alcohols, the applications of which range from starting materials for the syntheses of biologically active compounds to effective ligands in asymmetric transformations.

Exploitation of antagonistic electronic densities for the stereoselective reduction of ketones bearing masked amino surrogates

254th National Meeting (2017)

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