ArticleChemistry (Weinheim an der Bergstrasse, Germany)2013
The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 40 citations in OpenAlex.
- Metal Triflate-Promoted Allylic Substitution Reactions of Cinnamyl Alcohol in the Presence of Orthoesters and Acetals.ACS omega · 2019Article
- Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron(III) catalyst.Nature communications · 2019Article
- Chirality Transfer in Gold(I)-Catalysed Hydroalkoxylation of 1,3-Disubstituted Allenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives.ChemistryOpen · 2016Article
- Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Gold(I)-catalysed direct thioetherifications using allylic alcohols: an experimental and computational study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2014Article
- Gold(I) and Palladium(II) Complexes of 1,3,4-Trisubstituted 1,2,3-Triazol-5-ylidene "Click" Carbenes: Systematic Study of the Electronic and Steric Influence on Catalytic Activity.Organometallics · 2013Article
- Gold(I)-catalysed one-pot synthesis of chromans using allylic alcohols and phenols.Beilstein journal of organic chemistry · 2013Article
- Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses.Beilstein journal of organic chemistry · 2013Article
- Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives.Beilstein journal of organic chemistry · 2013Article
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2 authors at 2 institutions in 1 country.
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Abstract
A 1:1 mixture of [AuCl(IPr)] (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidine) and AgClO(4) catalyzes the intermolecular dehydrative alkoxylation of primary and secondary allylic alcohols with aliphatic primary and secondary alcohols to form allylic ethers. These transformations are regio- and stereospecific with preferential addition of the alcohol nucleophile at the γ-position of the allylic alcohol syn to the departing hydroxyl group and with predominant formation of the E stereoisomer. The minor α regioisomer is formed predominantly through a secondary reaction manifold involving regioselective γ-alkoxylation of the initially formed allylic ether rather than by the direct α-alkoxylation of the allylic alcohol.
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