ja8b02751_si_001.pdf (11.68 MB)
Download fileFormation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers
journal contribution
posted on 2018-04-17, 00:00 authored by Harshkumar
H. Patel, Matthew B. Prater, Scott O. Squire, Matthew S. SigmanThis report details a palladium-catalyzed
process to access highly
functionalized, optically active allylic aryl ethers. A number of
electron-deficient alkenyl triflates underwent enantioselective
and site-selective coupling with acyclic aryl enol ethers in the presence
of a chiral palladium catalyst. This transform provides chiral allylic
ether products in high yields and excellent enantiomeric ratios, furnishing
a unique disconnection to incorporate heteroatoms at a stereocenter.
Finally, the applicability of the products to target synthesis was
demonstrated through the formation of a chiral allylic alcohol and
the generation of a flavone-inspired product.
History
Usage metrics
Read the peer-reviewed publication
Categories
Keywords
Acyclic Enol Etherschiral allylic ether productsenantiomeric ratiosflavone-inspired productchiral palladium catalystallylic aryl ethersreport detailsChiral Allylic Ethersacyclic aryl enol etherstarget synthesisEnantioselective Palladium-Catalyzed Alkenylationpalladium-catalyzed processformationchiral allylic alcoholelectron-deficient alkenyl triflates