Aminoalcohol Synthesis through Nonprecious Metal Catalysis: Enantioselective Cu-Catalyzed Reductive Coupling of Aldehydes and Allenamides

Herein, we report the development of a Cu-catalyzed aminoallylation of aldehyde electrophiles through reductive coupling by circumventing the problematic competitive reduction of the aldehyde electrophile by a CuH catalyst. This leads to a highly diastereo- and enantioselective process for the synthesis of chiral 1,2-aminoalcohols containing secondary alcohol substitution. Cleavage of the N substituents on the reaction products was performed, allowing access to the other diastereomer of the aminoalcohol, which was investigated in the context of a synthesis of eligulstat.