Total Syntheses of Basiliolide A1, Basiliolide A2, Basiliolide C, and their Structural Analogues
Sign Up to like & getrecommendations! Published in 2018 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.201701211
Abstract: A small focus library of basiliolides including basiliolide A₁, basiliolide A₂, basiliolide C and their structural analogues have been prepared for the structure-activity relationship study. The synthesis features a cyclopropanation/ring-opening strategy for establishing the C8… read more here.
Keywords: cyclopropanation; total syntheses; structural analogues; basiliolide structural ... See more keywords
Asymmetric Radical Cyclopropanation of Dehydroaminocarboxylates: Stereoselective Synthesis of Cyclopropyl α-Amino Acids.
Sign Up to like & getrecommendations! Published in 2021 at "Chem"
DOI: 10.1016/j.chempr.2021.03.002
Abstract: A catalytic radical process has been developed for asymmetric cyclopropanation of dehydroaminocarboxylates with in situ-generated α-aryldiazomethanes via Co(II)-based metalloradical catalysis (MRC). Through fine-tuning the environments of D 2-symmetric chiral amidoporphyrin platform as the supporting ligands,… read more here.
Keywords: stereoselective synthesis; amino; cyclopropanation dehydroaminocarboxylates; cyclopropanation ... See more keywords
Theoretical Insights into the Mechanism and Stereoselectivity of Olefin Cyclopropanation Catalyzed by Two Engineered Cytochrome P450 Enzymes.
Sign Up to like & getrecommendations! Published in 2018 at "Inorganic chemistry"
DOI: 10.1021/acs.inorgchem.8b01875
Abstract: Engineered P450s can catalyze some non-natural reactions with high efficiency and excellent selectivity, such as the carbine transfer, nitrene transfer, C-H insertion, and C-H amination, opening alternative routes for sustainable production of chemicals. Recent experiments… read more here.
Keywords: cyclopropanation; two engineered; engineered cytochrome; cytochrome p450 ... See more keywords
Organocatalytic Cyclopropanation of (E)-Dec-2-enal: Synthesis, Spectral Analysis and Mechanistic Understanding
Sign Up to like & getrecommendations! Published in 2018 at "Journal of Chemical Education"
DOI: 10.1021/acs.jchemed.7b00566
Abstract: An undergraduate experiment combining synthesis, NMR analysis and mechanistic understanding is reported. The students perform an organocatalyzed cyclopropanation reaction of (E)-dec-2-enal and are then required to determine the diastereoselectivity and assign the relative configuration of… read more here.
Keywords: cyclopropanation; dec enal; analysis mechanistic; mechanistic understanding ... See more keywords
Enabling Cyclopropanation Reactions of Imidazole Heterocycles via Chemoselective Photochemical Carbene Transfer Reactions of NHC-Boranes.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00609
Abstract: Herein we report a site-selective cyclopropanation of N-heterocyclic carbene (NHC)-borane complexes via photochemical carbene transfer reactions. By subtle changes to the reaction conditions, this approach can be further extended toward the difunctionalization of NHC-boranes via… read more here.
Keywords: carbene transfer; transfer reactions; photochemical carbene; cyclopropanation ... See more keywords
Synthesis of Aryl Perfluorocyclopropyl Ethers via [2 + 1] Cyclopropanation Using TMSCF2Br Reagent.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00958
Abstract: Aryl perfluorocyclopropyl ethers have been synthesized for the first time by [2 + 1] cyclopropanation between aryl trifluorovinyl ethers and a commercially available TMSCF2Br reagent. This cycloaddition reaction between two fluorine-containing reactants proceeds smoothly in… read more here.
Keywords: aryl perfluorocyclopropyl; tmscf2br reagent; perfluorocyclopropyl ethers; cyclopropanation ... See more keywords
Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α-Carbonyl Sulfoxonium Ylides
Sign Up to like & getrecommendations! Published in 2022 at "Organic Letters"
DOI: 10.1021/acs.orglett.2c03396
Abstract: Enantioselective cyclopropanation of α-carbonyl sulfoxonium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular cyclopropanation of SY in the presence of a chiral diene… read more here.
Keywords: cyclopropanation carbonyl; iridium; carbonyl sulfoxonium; cyclopropanation ... See more keywords
Access to Optically Active 7-Membered Rings by a 2-Step Synthetic Sequence: Cu-Catalyzed Stereoselective Cyclopropanation of Branched 1,3-Dienes/Rh-Catalyzed Stereoconvergent [5 + 2] Cycloaddition
Sign Up to like & getrecommendations! Published in 2020 at "ACS Catalysis"
DOI: 10.1021/acscatal.0c02956
Abstract: We report a 2-step cyclopropanation/cycloaddition catalytic sequence that provides access to optically active 7-membered rings with a carboxyl-bearing tertiary stereocenter. In the first step, the ... read more here.
Keywords: optically active; membered rings; cyclopropanation; cycloaddition ... See more keywords
Combined Experimental and Computational Study of Ruthenium N-Hydroxyphthalimidoyl Carbenes in Alkene Cyclopropanation Reactions
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DOI: 10.1021/acscatal.1c02540
Abstract: A combined experimental–computational approach has been used to study the cyclopropanation reaction of N-hydroxyphthalimide diazoacetate (NHPI-DA) with various olefins, catalyzed by a ruthenium-phenyloxazoline (Ru-Pheox) complex. Kinetic studies show that the better selectivity of the employed… read more here.
Keywords: cyclopropanation; ruthenium; study; experimental computational ... See more keywords
Stereoselectivity, Different Oxidation States, and Multiple Spin States in the Cyclopropanation of Olefins Catalyzed by Fe–Porphyrin Complexes
Sign Up to like & getrecommendations! Published in 2018 at "ACS Catalysis"
DOI: 10.1021/acscatal.8b01492
Abstract: The mechanism of the cyclopropanation of alkenes with diazocompounds catalyzed by ClFeIII–porphyrin, [ClFeII–porphyrin]−, and FeII–porphyrin has been investigated by density functional theory calculations. The obtained results indicate that the only viable catalyst is the FeII–porphyrin,… read more here.
Keywords: cyclopropanation; spin states; different oxidation; porphyrin ... See more keywords
DFT Mechanistic Study of the Cyclopropanation of Styrene and Aryldiazodiacetate Catalyzed by Tris(pentafluorophenyl)borane
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DOI: 10.1021/acsomega.2c00200
Abstract: Metal-free boron Lewis acids, tris(pentafluorophenyl)borane B(C6F5)3, have the advantages of low toxicity and low cost and are a promising catalyst. A density functional theory (DFT) calculation was used to clarify the mechanism and the origin… read more here.
Keywords: styrene; pentafluorophenyl borane; cyclopropanation; mechanism ... See more keywords