Sep 2021 News Something interesting about 2-(4-Methoxyphenyl)dihydro-2H-pyran-4(3H)-one

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A series of monodeuterated benzylic and allylic ethers were subjected to oxidative carbon-hydrogen bond cleavage to determine the impact of structural variation on intramolecular kinetic isotope effects in DDQ-mediated cyclization reactions. These values are compared to the corresponding intermolecular kinetic isotope effects that were accessed through subjecting mixtures of non-deuterated and dideuterated substrates to the reaction conditions. The results indicate that carbon-hydrogen bond cleavage is rate determining and that a radical cation is most likely a key intermediate in the reaction mechanism.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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A novel self-terminated Prins strategy has been developed for the synthesis of 2-substituted tetrahydropyran-4-one derivatives through a condensation of 3-(phenylthio)but-3-en-1-ol with carbonyl compounds in the presence of 5 mol% of Sc(OTf)3 under mild conditions. A few products were subsequently transformed into the corresponding indoles by Fisher-indole synthesis.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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A novel self-terminated Prins strategy has been developed for the synthesis of 2-substituted tetrahydropyran-4-one derivatives through a condensation of 3-(phenylthio)but-3-en-1-ol with carbonyl compounds in the presence of 5 mol% of Sc(OTf)3 under mild conditions. A few products were subsequently transformed into the corresponding indoles by Fisher-indole synthesis.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Enantioselective reduction of 2-substituted tetrahydropyran-4-ones using Daucus carota plant cells

Enzymatic reduction of 2-substituted tetrahydropyran-4-ones with Daucus carota, plant cells as biocatalyst occurred in water under extremely mild and environmentally benign conditions giving a 1:1 mixture of diastereoselectively (2R,4S)- and (2S,4S)-2-aryl- or 2-alkyl-tetrahydropyranols in high yields.

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Tetrahydropyran – Wikipedia,
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2,3-dichloro-5,6-dicyano-1,4-benzoquinone-catalyzed teactions employing MnO2 as a stoichiometric oxidant

Several oxidative reactions can be effected with MnO2 in the presence of substoichiometric quantities of DDQ. These transformations include oxidative cyclization, deprotection, and dehydrogenation reactions. The use of MnO2 as a terminal oxidant for DDQ-mediated reactions is attractive based on economical and environmental factors.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics