1579249-54-9Relevant academic research and scientific papers
Enantioselective Synthesis of Di- and Tri-Arylated All-Carbon Quaternary Stereocenters via Copper-Catalyzed Allylic Arylations with Organolithium Compounds
Guduguntla, Sureshbabu,Gualtierotti, Jean-Baptiste,Goh, Shermin S.,Feringa, Ben L.
, p. 6591 - 6595 (2016/10/18)
The highly enantioselective copper(I)/N-heterocyclic carbene (NHC) catalyzed synthesis of di- and triarylated all-carbon quaternary stereocenters via asymmetric allylic arylation (AAAr) with aryl organolithium compounds is demonstrated. The use of readily available or easily accessible aryl organolithium reagents in combination with trisubstituted allyl bromides, in the presence of a copper/NHC catalyst, affords important di- and triarylated all-carbon quaternary stereocenters in good yields and enantioselectivities. This method tolerates a wide range of alkyl and substituted aryl groups in the starting allyl bromides, including less common biaryl moieties, which, in combination with diverse organolithium reagents, delivers a broad scope of products in an operationally straightforward and efficient manner.
Synthesis of quaternary carbon stereocenters by copper-catalyzed asymmetric allylic substitution of allyl phosphates with arylboronates
Takeda, Momotaro,Takatsu, Keishi,Shintani, Ryo,Hayashi, Tamio
, p. 2354 - 2367 (2014/04/17)
A copper-catalyzed asymmetric allylic substitution of γ,γ- disubstituted allyl phosphates with arylboronates has been developed for the construction of quaternary stereocenters. High regio- and enantioselectivities have been achieved by employing a hydroxy-bearing chiral N-heterocyclic carbene ligand, and both E and Z substrates provide the same enantiomer as the major product. The mechanistic aspect of this catalysis has also been investigated to find that a 1:1 copper/ligand complex is most likely responsible for the present asymmetric catalysis, and the reaction proceeds with almost perfect 1,3-anti stereochemistry with respect to the allylic electrophile.
