Enantioselective α-functionalizations of ketones via allylic substitution of silyl enol ethers
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منابع مشابه
Iridium-catalyzed enantioselective allylation of silyl enol ethers derived from ketones and α,β-unsaturated ketones.
The unified Ir-catalyzed enantioselective allylic substitution reactions of silyl enol ethers derived from ketones and α,β-unsaturated ketones with branched, racemic allylic alcohols are described. This transformation is catalyzed by the Carreira system and proceeds without fluoride, and with high ee and b : l ratio. The synthetic utility of this method was illustrated by the concise enantiosel...
متن کاملChiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones.
A chiral Brønsted acid has been developed from a cationic gold(I) disphosphine complex in the presence of alcoholic solvent and applied to the enantioselective protonation reaction of silyl enol ethers of ketones. Various optically active cyclic ketones were obtained in excellent yields and high enantioselectivities, including cyclic ketones bearing aliphatic substrates at the α-position. Furth...
متن کاملalpha-Nitration of Ketones via Enol Silyl Ethers. Radical Cations as Reactive Intermediates in Thermal and Photochemical Processes.
Highly colored (red) solutions of various enol silyl ethers and tetranitromethane (TNM) are readily bleached to afford good yields of alpha-nitro ketones in the dark at room temperature or below. Spectral analysis show the red colors to be associated with the intermolecular 1:1 electron donor-acceptor (EDA) complexes between the enol silyl ether and TNM. The formation of similar vividly colored...
متن کاملRegio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates.
The Pd-catalyzed reorganization of enol allyl carbonates to allylated ketones occurs asymmetrically in the presence of chiral ligands previously developed in this group. With 2-methylcyclohexanone, asymmetric regioselective alkylation occurs at the more substituted carbon without complications of polyalkylation. Alkylation to create quaternary centers in indanones and benzonabenone occurs in mu...
متن کاملRadical 1,2-aryl migration in α,α-diaryl allylic alcohols toward β-silyl ketones.
A copper-catalyzed radical 1,2-aryl migration in α,α-diaryl allylic alcohols is developed, leading to β-silyl carbonyl compounds in moderate to good yields. The migration of aryls with lower aromaticity is favored. This procedure features the employment of silanes as commercially available materials.
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ژورنال
عنوان ژورنال: Nature Chemistry
سال: 2018
ISSN: 1755-4330,1755-4349
DOI: 10.1038/s41557-018-0165-x