Topic
Alkylation
About: Alkylation is a research topic. Over the lifetime, 29915 publications have been published within this topic receiving 464944 citations. The topic is also known as: alkylation reaction.
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TL;DR: In this article, a method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and alpha,beta-unsaturated carboxylic esters that bear a gamma-phosphate is reported.
Abstract: A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and alpha,beta-unsaturated carboxylic esters that bear a gamma-phosphate is reported. These transformations afford alpha-alkyl-beta,gamma-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (S(N)2':S(N)2) and in 87-97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.
88 citations
TL;DR: In this article, the reaction of phenol with methanol was carried out over five X-, six Y- and three ZSM-zeolites, in a fixed-bed continuous reactor at 250°C.
88 citations
TL;DR: An amide-derived N,N,N-Fe(II) complex was used to catalyse the hydroboration of alkenes at room temperature in this article, where the alkylation of a remote site on the ligand backbone was used as a late-stage modification to provide a more electrophilic complex as determined by electrochemical studies.
Abstract: An amide-derived N,N,N-Fe(II) complex catalyzes the hydroboration of alkenes at room temperature. Alkylation of a remote site on the ligand backbone was used as a late-stage modification to provide a more electrophilic complex as determined by electrochemical studies. The alkylated variant, compared to the parent complex, catalyzes olefin hydroboration with an increased reaction rate and exhibits distinct regioselectivity for internal alkene hydroboration.
88 citations
TL;DR: It is shown that alpha,alpha-disubstituted pseudoephedrine amide enolates can be generated in a highly stereocontrolled fashion by conjugate addition of an alkyllithium reagent to the s-cis-conformer of an alpha-alkyl-alpha,beta-unsaturated pseudoephernylbutyramides that undergo alkylation in the same sense as those formed by direct deprotonation.
Abstract: Protocols for the stereodefined formation of α,α-disubstituted enolates of pseudoephedrine amides are presented followed by the implementation of these in diastereoselective alkylation reactions. Direct alkylation of α,α-disubstituted pseudoephedrine amide substrates is demonstrated to be both efficient and diastereoselective across a range of substrates, as exemplified by alkylation of the diastereomeric pseudoephedrine α-methylbutyramides, where both substrates are found to undergo stereospecific replacement of the α-C−H bond with α-C−alkyl, with retention of stereochemistry. This is shown to arise by sequential stereospecific enolization and alkylation reactions, with the alkyl halide attacking a common π-face of the E- and Z-enolates, proposed to be opposite the pseudoephedrine alkoxide side chain. Pseudoephedrine α-phenylbutyramides are found to undergo highly stereoselective but not stereospecific α-alkylation reactions, which evidence suggests is due to facile enolate isomerization. Also, we show t...
88 citations
TL;DR: The tris(acetylacetonato)rhodium(III) catalyst is shown to be a versatile catalyst in the presence of DABCO (1,4-diazabicyclo[2.2]octane) as ligand for the α-alkylation of ketones followed by transfer hydrogenation, for the one-pot β-alkyation of secondary alcohols with primary alcohols and for the alkylation of aromatic amines in the absence of an inorganic base in toluene as discussed by the authors.
Abstract: The tris(acetylacetonato)rhodium(III) catalyst is shown to be a versatile catalyst in the presence of DABCO (1,4-diazabicyclo[2.2.2]octane) as ligand for the α-alkylation of ketones followed by transfer hydrogenation, for the one-pot β-alkylation of secondary alcohols with primary alcohols and for the alkylation of aromatic amines in the presence of an inorganic base in toluene.
88 citations