Regio- and Diastereoselective Decarboxylative Allylation of N-Aryl α-Amino Acids by Dual Photoredox/Nickel Catalysis

Homoallylic amines are important building blocks for the synthesis of nitrogen-containing natural products. They are generally synthesized by addition of ally! metal compounds to imines. With the establishment of photoredox catalysis in organic chemistry, research interest in homoallylic amine syntheses via radical reactions has increased. Herein, we present a dual photoredox/nickel catalyzed regio- and diastereoselective allylation reaction of N-aryl alpha-amino acids. Our method yields branched homoallylic amines in high yields and high syn-diastereoselectivity under mild and redox-neutral conditions. The synthetic flexibility of our reaction is demonstrated in a broad substrate scope, which is characterized by a high functional group tolerance. Detailed mechanistic studies revealed an imine as the key intermediate in this reaction.

Automated summary

A dual photoredox/nickel catalyzed method for the regio- and diastereoselective allylation of N-aryl alpha-amino acids is presented. The reaction provides branched homoallylic amines in high yields and high syn-diastereoselectivity under mild and redox-neutral conditions. The broad substrate scope and high functional group tolerance demonstrate the synthetic flexibility of this reaction.