Keary Engle - Professor Product Portal

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Professor Keary Engle

The Engle lab strives to invent novel catalytic alkene and alkyne functionalization methods to expedite organic synthesis. These transformations offer a powerful platform for conversion of simple, abundant, and planar starting materials into densely functionalized, stereochemically complex products in a single step. To this end, the Engle lab has developed various substrate directivity strategies in which native functional groups can be temporarily masked with auxiliaries that are capable of reversibly binding the metal catalyst, thereby enhancing kinetic reactivity, suppressing unwanted side reactions, and facilitating high selectivity. The Engle lab works with us to make synthetically enabling directing groups, catalysts, and ligands readily available to the synthetic community for reaction discovery and small-molecule synthesis.

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Miriam L O'Duill, Rei Matsuura, Yanyan Wang, Joshua L Turnbull, John A Gurak, De-Wei Gao, Gang Lu, Peng Liu, Keary M Engle
Journal of American Society 2017-10-03
Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful...Read More
Zhen Liu, Tian Zeng, Kin S. Yang, and Keary M. Engle
Journal of American Society 2016-10-25
A palladium(II)-catalyzed 1,2-dicarbofunctionalization reaction of unactivated alkenes has been developed, wherein a cleavable bidentate directing group is used to control the regioselectivity and stabilize the putative alkylpalladium(II) intermediate. Under the optimized reaction conditions, a broad range of nucleophiles...Read More
John A. Gurak Jr., Kin S. Yang, Zhen Liu, and Keary M. Engle
Journal of American Society 2016-04-16
A directed, regiocontrolled hydroamination of unactivated terminal and internal alkenes is reported. The reaction is catalyzed by palladium(II) acetate and is compatible with a variety of nitrogen nucleophiles. A removable bidentate directing group is used to control the regiochemistry, prevent β-hydride elimination, and stabilize...Read More