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A Transient Directing Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes

preprint
submitted on 12.09.2019, 05:57 and posted on 12.09.2019, 16:59 by Lucas Oxtoby, Zi-Qi Li, Van Tran, Tuğçe Erbay, Ruohan Deng, Peng Liu, Keary Engle

Metal-coordinating directing groups have seen extensive use in the field of transition-metal-mediated functionalization of alkenes; however, their waste-generating installation and removal steps limit the efficiency and practicality of reactions that rely on their use. Inspired by developments in the field of C–H activation, herein we report a transient directing group approach to reductive Heck hydroarylation of alkenyl benzaldehyde substrates that proceeds under mild conditions. Highly stereoselective migratory insertion is facilitated by in situ formation of an imine from catalytic amounts of commercially available amino acid additive. Computational studies reveal an unusual mode of enantioinduction by the remote chiral center in the transient directing group.

Funding

NSF/DGE-184247

NIH-R35GM125052

NIH-R35GM128779

Alfred P. Sloan Fellowship

Camille Dreyfus Teacher Scholar Award

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

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