Enantioselective Synthesis of Atropisomers via Vinylidene ortho-Quinone Methides (VQMs).
Sign Up to like & getrecommendations! Published in 2022 at "Accounts of chemical research"
DOI: 10.1021/acs.accounts.2c00486
Abstract: ConspectusAtropisomers, arising from conformational restriction, are inherently chiral due to the intersecting dissymmetric planes. Since there are numerous applications of enantiopure atropisomers in catalyst design, drug discovery, and material science, the asymmetric preparation of these… read more here.
Keywords: enantioselective synthesis; chemistry; vinylidene ortho; synthesis ... See more keywords
Harnessing ortho-Quinone Methides in Natural Product Biosynthesis and Biocatalysis.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of natural products"
DOI: 10.1021/acs.jnatprod.1c01026
Abstract: The implementation of ortho-quinone methide (o-QM) intermediates in complex molecule assembly represents a remarkably efficient strategy designed by Nature and utilized by synthetic chemists. o-QMs have been taken advantage of in biomimetic syntheses for decades,… read more here.
Keywords: quinone methides; harnessing ortho; methides natural; product ... See more keywords
Nonenzymatic Self-Assembly Access to Diverse ortho-Quinone Methide-Based Pseudonatural Products.
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DOI: 10.1021/acs.orglett.2c02268
Abstract: A nonenzymatic self-assembly program was introduced to explore diverse clavatol-based pseudonatural products (PNPs) in a marine-derived fungus. Intermolecular couplings of the chemoreactive ortho-quinone methide of clavatol with native acceptors led to 14 clavatol-based PNPs with… read more here.
Keywords: nonenzymatic self; based pseudonatural; self assembly; pseudonatural products ... See more keywords
Dissolution of the Heteroatom Dopants and Formation of Ortho-Quinone Moieties in the Doped Carbon Materials during Water Electrooxidation.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.1c13374
Abstract: Heteroatom-doped carbon materials are widely used as metal-free electrocatalysts and supporting substrates for many metal-based composites. However, almost all the current researches are based on the assumption of the self-stability of the heteroatom-doped carbon materials,… read more here.
Keywords: doped carbon; heteroatom doped; ortho quinone; carbon ... See more keywords
Modification of N-terminal α-amine of proteins via biomimetic ortho-quinone-mediated oxidation
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DOI: 10.1038/s41467-021-22654-7
Abstract: Naturally abundant quinones are important molecules, which play essential roles in various biological processes due to their reduction potential. In contrast to their universality, the investigation of reactions between quinones and proteins remains sparse. Herein,… read more here.
Keywords: ortho quinone; quinone mediated; via biomimetic; quinone ... See more keywords
Phosphine-mediated enantioselective [4 + 1] annulations between ortho-quinone methides and Morita–Baylis–Hillman carbonates
Sign Up to like & getrecommendations! Published in 2018 at "Organic chemistry frontiers"
DOI: 10.1039/c8qo00487k
Abstract: The first example of phosphine catalyzed enantioselective [4 + 1] annulations of ortho-quinone methides and Morita–Baylis–Hillman carbonates is described. In the presence of 1,2-bis[(2R,5R)-2,5-dimethylphospholano]benzene monoxide, Morita–Baylis–Hillman carbonates reacted with ortho-quinone methides smoothly to afford a… read more here.
Keywords: ortho quinone; morita baylis; quinone methides; baylis hillman ... See more keywords
Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines.
Sign Up to like & getrecommendations! Published in 2020 at "Chemical communications"
DOI: 10.1039/d0cc00747a
Abstract: A [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with formaldimines is described for the synthesis of perfluoroalkylated tetrahydroquinazolines. Key to this process is the photocatalytic radical-mediated generation of aza-o-QMs from 2-vinylanilines and perfluoroalkyl radical precursors as… read more here.
Keywords: photogenerated aza; ortho quinone; aza ortho; cycloaddition photogenerated ... See more keywords
A new cycloaddition profile for ortho-quinone methides: photoredox-catalyzed [6+4] cycloadditions for synthesis of benzo[b]cyclopenta[e]oxepines.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d1cc06332d
Abstract: Visible-light-induced [6+4] cycloaddition reactions of ortho-quinone methides have been developed. The reaction of ortho-quinone methides with pentafulvenes in the presence of a thioxanthylium photoredox catalyst afforded benzo[b]cyclopenta[e]oxepines. The present reaction represents a promising tool for… read more here.
Keywords: cyclopenta oxepines; benzo cyclopenta; quinone methides; ortho quinone ... See more keywords
Stereoselective Reactions of ortho-Quinone Methide and ortho-Quinone Methide Imines and Their Utility in Natural Product Synthesis
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DOI: 10.1055/s-0037-1610241
Abstract: Herein presented is a review of the reactivity and synthetic utility of ortho-quinone methides and ortho-quinone methide imines. These versatile intermediates have received significant attention in the literature and new methods for their preparation and… read more here.
Keywords: quinone methide; ortho quinone; utility; methide imines ... See more keywords
Vinylidene ortho-Quinone Methides: Unique Chiral Reaction Intermediates in Catalytic Asymmetric Synthesis.
Sign Up to like & getrecommendations! Published in 2018 at "Chimia"
DOI: 10.2533/chimia.2018.892
Abstract: Vinylidene ortho-quinone methides (VQMs) are one-carbon elongated homologues of ortho-quinone methides (QMs), well-known as useful reaction intermediates in organic transformations. These related quinone methides are quite distinct in terms of stereochemistry. Namely, VQMs are characterized… read more here.
Keywords: ortho quinone; reaction intermediates; vinylidene ortho; quinone methides ... See more keywords
Detection of Bacterial α-l-Fucosidases with an Ortho-Quinone Methide-Based Probe and Mapping of the Probe-Protein Adducts
Sign Up to like & getrecommendations! Published in 2022 at "Molecules"
DOI: 10.3390/molecules27051615
Abstract: Fucosidases are associated with several pathological conditions and play an important role in the health of the human gut. For example, fucosidases have been shown to be indicators and/or involved in hepatocellular carcinoma, breast cancer,… read more here.
Keywords: probe; methide based; ortho quinone; quinone methide ... See more keywords