Chemo- and Enantioselective Reduction of α-Keto Amides to α-Hydroxy Amides using Reusable CuO-Nanoparticles as Catalyst

An efficient, commercially available, and reusable copper-oxide nanoparticle (CuO-NPs) and (R)-(-)-DTBM SEGPHOS catalyzed chemo-and enantioselective reduction of alpha-keto amides to alpha-hydroxy amides has been developed. The scope of the reaction has been studied with various alpha-keto amides containing electron-donating and electron-withdrawing groups affording the enantiomerically enriched alpha-hydroxy amides in good yields with excellent enantioselectivity. The CuO-NPs catalyst has been recovered and reused up to four catalytic cycles without any significant change in particle size, reactivity, and enantioselectivity.

Automated summary

An efficient and reusable catalyst composed of copper-oxide nanoparticles and (R)-(-)-DTBM SEGPHOS has been developed for the chemo- and enantioselective reduction of alpha-keto amides to alpha-hydroxy amides. The reaction showed excellent enantioselectivity and good yields for various alpha-keto amides containing different electron-donating and electron-withdrawing groups. The copper-oxide nanoparticle catalyst maintained its size, reactivity, and enantioselectivity after being reused for four catalytic cycles.