Unknown

Dataset Information

0

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

Json Xml
altmetric image

Publications

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]

Similar Datasets

Unknown Palladium-Catalyzed Enantioselective Alkenylation of Enelactams Using a Relay Heck Strategy.
| S-EPMC6731067 | biostudies-literature
Unknown Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers.
| S-EPMC5152571 | biostudies-literature
Unknown Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.
| S-EPMC4785804 | biostudies-literature
Unknown Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers.
| S-EPMC5968819 | biostudies-literature
Unknown Palladium-Catalyzed Enantioselective Heck Alkenylation of Trisubstituted Allylic Alkenols: A Redox-Relay Strategy to Construct Vicinal Stereocenters.
| S-EPMC5395252 | biostudies-literature
Unknown Palladium-Catalyzed, Enantioselective Heine Reaction.
| S-EPMC4933940 | biostudies-literature
Unknown Palladium-Catalyzed Selective ?-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.
| S-EPMC4887130 | biostudies-literature
Unknown Enantioselective Palladium-Catalyzed Oxidative β,β-Fluoroarylation of α,β-Unsaturated Carbonyl Derivatives.
| S-EPMC6482284 | biostudies-literature
Unknown Enantioselective alkenylation via nickel-catalyzed cross-coupling with organozirconium reagents.
| S-EPMC2860276 | biostudies-literature
Unknown Enantioselective Synthesis of Alkyl Allyl Ethers via Palladium-Catalyzed Redox-Relay Heck Alkenylation of <i>O</i>-Alkyl Enol Ethers.
| S-EPMC7806183 | biostudies-literature