Gold and Biocatalysis for the Stereodivergent Synthesis of Nor(pseudo)ephedrine Derivatives: Cascade Design Toward Amino Alcohols, Diols, and Diamines

The combination of gold(I) and enzyme catalysis has provided access to a series nor(pseudo)ephedrine derivatives in regio- stereoselective manner. approach involves developing IPrAuNTf2-catalyzed hydration 1-phenylprop-2-yn-1-yl acetate or N-(1-phenylprop-2-yn-1-yl)acetamide, followed by (dynamic) asymmetric biotransamination bioreduction the corresponding keto ester amide intermediates. Enzyme actions were completely selective towards modification methyl ketones highly manner, allowing synthesis enantio- diastereomerically enriched products using either racemic optically active starting materials. Thus, amino alcohol, diol, diamine produced from propargyl esters amides (57 86% isolated yield), biocatalyst choice determining (stereo)selectivity overall cascade process (70–99% diastereomeric excess >98% enantiomeric excess), providing compounds straightforward