A while back we observed formation of an unexpected byproduct in an attempted screen of various ketone-based transient directing groups (TDGs) for metal-catalyzed difunctionalization of ortho-alkenylaniline substrates. After initial condensation to form the corresponding ketimine, cyclization took place to furnish the corresponding dihydro-1-benzazepines. Recognizing the utility of the products, we optimized high-yielding reaction conditions, explored the scope and limitations of the method, and evaluated the potential of the products as ligands for transition metals. We are pleased to share the culmination of these efforts this week in Tetrahedron Letters as part of a special issue celebrating Prof. Song Lin’s Tetrahedron Young Investigator Award. Hats off to Alena and Jose for invaluable preliminary data and Letian and Juntao for getting the project to the finish line.

For a link to the paper in Tetrahedron Letters, click here: https://www.sciencedirect.com/science/article/pii/S0040403925001212