Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles
نویسندگان
چکیده
منابع مشابه
Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.
The first enantioselective aldehyde α-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantiosele...
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Detailed herein is the photochemical organocatalytic enantioselective α-alkylation of aldehydes with (phenylsulfonyl)alkyl iodides. The chemistry relies on the direct photoexcitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground-state chiral enamines provide effective stereochemical control over the radical trapping process. The ph...
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A chiral cobalt-catalyzed enantioselective aerobic oxidative kinetic resolution of (±)-α-hydroxy esters, using molecular oxygen as a sole oxidant, is reported and a maximum of selectivity factor (s) 31.9 was achieved with >99% enantiomeric excess for unreacted α-hydroxy esters.
متن کاملIron-catalyzed N-alkylation using π-activated ethers as electrophiles.
A new method for the synthesis of diverse N-alkylation compounds was developed via an iron-catalyzed etheric C(sp(3))-O cleavage with the C-N bond formation in the reaction of π-activated ethers with various nitrogen-based nucleophiles. In addition, the mechanism of this reaction was investigated.
متن کاملSpin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols.
Nature routinely engages alcohols as leaving groups, as DNA biosynthesis relies on the removal of water from ribonucleoside diphosphates by a radical-mediated "spin-center shift" (SCS) mechanism. Alcohols, however, remain underused as alkylating agents in synthetic chemistry due to their low reactivity in two-electron pathways. We report herein an enantioselective α-benzylation of aldehydes usi...
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ژورنال
عنوان ژورنال: Angewandte Chemie International Edition
سال: 2018
ISSN: 1433-7851
DOI: 10.1002/anie.201806742