Chiral amines are important functional moieties found in many natural products, pharmaceutical drugs, and agrochemicals. The asymmetric 1,2-addition of carbon-nucleophiles to imine derivatives is an especially powerful synthesis towards chiral amines, but electrochemical approaches are not well explored. An electrochemical approach from <i>N</i>-sulfinyl imines for the synthesis of chiral amines has the potential to expand both the versatility of <i>N</i>-sulfinyl imines and the rapidly developing field of electrochemical organic synthesis. A novel and practical electrochemical approach for the synthesis of chiral amines and amino acid derivatives was developed. Significant solvent and Lewis acid effects were observed, greatly improving both diastereoselectivity (up to &gt;20:1) and yields (up to 95%). A broad substrate scope was obtained, with tertiary alkyl, allylic, aryl, and heterocycle-containing amine products achieving high yields and diastereoselectivity. Future work includes expanding the range of carbon-based nucleophilic coupling partners and elaboration of the new methodology in large scale and total synthesis of chiral amine containing drugs.

Electrochemical synthesis of chiral amines and amino acid derivatives

ACS Spring 2022

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