Enantioselective Copper-Catalyzed 1,5-Cyanotrifluoromethylation of Vinylcyclopropanes.

Org Lett

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, Center for Excellence in Molecular Synthesis of CAS , University of Science and Technology of China, 96 Jinzhai Road , Hefei , Anhui 230026 , China.

Published: October 2019

AI Article Synopsis

  • - A new method has been created for a specific chemical reaction called copper-catalyzed 1,5-cyanotrifluoromethylation, which involves a radical relay strategy using vinylcyclopropanes.
  • - This reaction shows high levels of enantioselectivity (how well it can produce one specific form of a molecule over another), can work with a variety of starting materials, and occurs under mild conditions.
  • - The process starts with generating a CF radical from Togni's reagent, providing a fresh way to create specialized chiral compounds that contain CF groups in their structure.

Article Abstract

A copper-catalyzed enantioselective 1,5-cyanotrifluoromethylation of vinylcyclopropanes has been developed using a radical relay strategy. This asymmetric reaction has demonstrated high enantioselective control, broad substrate scope, and mild conditions. Initiated by the generated CF radical from Togni's reagent, this method offers a new solution for remote enantioselective bifunctionalization of alkenes and thus provides a straightforward way for the synthesis of chiral CF-containing internal alkenylnitriles.

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Source
http://dx.doi.org/10.1021/acs.orglett.9b03012DOI Listing

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