Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives

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Abstract

A regioselective and enantioselective palladium-catalyzed relay Heck alkenylation of alkenylbenzene derivatives to construct remote stereocenters is disclosed. Various β-substituted styrenes were readily obtained in moderate yields with good to excellent levels of enantioselectivity. This strategy provides rapid access to enantioenriched δ, ϵ, ζ, and η-alkenyl aryl compounds from simple starting materials. Mechanistic studies suggest that termination of the relay reaction is controlled by affinity of the arene for the Pd complex during migration.

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Chen, Z. M., Liu, J., Guo, J. Y., Loch, M., Deluca, R. J., & Sigman, M. S. (2019). Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives. Chemical Science, 10(30), 7246–7250. https://doi.org/10.1039/c9sc02380a

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