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Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives.

ABSTRACT: A regioselective and enantioselective palladium-catalyzed relay Heck alkenylation of alkenylbenzene derivatives to construct remote stereocenters is disclosed. Various ?-substituted styrenes were readily obtained in moderate yields with good to excellent levels of enantioselectivity. This strategy provides rapid access to enantioenriched ?, ?, ?, and ?-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.

SUBMITTER: Chen ZM

PROVIDER: S-EPMC6685350 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives.

Chen Zhi-Min ZM Liu Jianbo J Guo Jing-Yao JY Loch Maximillan M DeLuca Ryan J RJ Sigman Matthew S MS

Chemical science 20190617 30

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 affini ...[more]

PMID: 31588293

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