During the past five years, our lab and others have demonstrated the power of directing auxiliaries in catalytic alkene functionalization. While highly enabling in their own right, these auxiliaries require additional steps for installation and removal, which detracts from their practical utility. In an effort to overcome this issue, we are excited to disclose the first successful demonstration of co-catalytic “transient” directing groups in asymmetric Heck-type migratory insertion in a paper that appears today in Angewandte Chemie International Edition. Under simple reaction conditions, a commercially available amino acid is able to reversibly condense with an aldehyde on the substrate and guide aryl addition to the β-position of the styrene-type substrate. Congrats to Luke, Zi-Qi, Van, and Ruohan from our lab; and our computational collaborator Tuğçe from the Liu Lab at the University of Pittsburgh. In case anyone missed it, a pre-print of this work was deposited in ChemRxiv back in September (click here).
For a link to the paper, see: https://onlinelibrary.wiley.com/doi/10.1002/anie.202001069