133572-04-0Relevant articles and documents
Iron-catalyzed stereospecific arylation of enol tosylates using Grignard reagents
Wei, Yi-Ming,Ma, Xiao-Di,Wang, Lei,Duan, Xin-Fang
, p. 1101 - 1104 (2020)
The stereospecific Fe-catalyzed arylation of enol tosylates was reported. Various tri- or tetrasubstituted Z or E-enol tosylates of β-keto esters were arylated using common and Knochel-type Grignard reagents with complete stereofidelity. The precursors fo
Enantioselective synthesis of all-carbon quaternary stereogenic centers via copper-catalyzed asymmetric allylic alkylation of (Z)-allyl bromides with organolithium reagents
Faans-Mastral, Martn,Vitale, Romina,Prez, Manuel,Feringa, Ben L.
, p. 4209 - 4212 (2015/03/14)
A copper/phosphoramidite catalyzed asymmetric allylic alkylation of Z trisubstituted allyl bromides with organolithium reagents is reported. The reaction affords all-carbon quaternary stereogenic centers in high yields and very good regio- and enantiosele
Single-isomer trisubstituted olefins from a novel reaction of (E)-βchloro-α-iodo-α,β-unsaturated esters and amides
Simard-Mercier, Julie,Jiang, Jojo Liu,Ho, Michael L.,Flynn, Alison B.,Ogilvie, William W.
, p. 5899 - 5906 (2008/12/21)
(Chemical Equation Presented) (E)-β-Chloro-α-iodo-α, β-unsaturated esters are converted to single isomer trisubstituted olefins bearing three different carbon substituents by cross-coupling under reflux. Mechanistic investigations suggest that this process transfers a hydrogen from the boronic acid to the α-position of the substrate and then introduces an aryl group to the β-position of the intermediate template while replacing chloride. The reaction is highly stereoselective, showing preference for the E-isomer. The process proceeds through (E)-β-chloro-α-aryl-α, β-unsaturated esters that are transformed efficiently into the corresponding E-products through stereoselective Suzuki-type reactions giving single isomers. The observed stereo-chemistry is apparently enabled by the intermediacy of a palladium allenoate. The reaction involves a catalytic cycle in which PdII is reduced to Pd0 through the formation of biaryl-coupled products.
