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Showing 1 to 20 of 48 for “"Allylation"”.
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Iridium-Catalyzed Enantioselective Allylation of Alkenyl Boronates
Organoboronic esters are highly functionalizable synthetic intermediates owing to their unique reactivity that allows for pre-complexation with organometallic reagents to form boronates, which can then engage in bimolecular reactions. Furthermore, incorporation of boronic esters into their …
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Lewis Base-Catalyzed Enantioselective Allylation and Aldol Addition Reactions
Embargo set by: Seth Robbins for item 85720 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs
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Brønsted acid-catalyzed stereoselective allylation of exo-glycals with allyltrimethylsilane
… exploit exo-glycals as starting materials. The allylation methodologies of sugar lactol and sugar lactone starting materials suffer from poor regio- and stereoselectivity. Recently, we have developed a synthetic method for the allylation of exo-glycals using allyltrimethylsilane. This Brønsted …
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Chiral-Phosphoramide-Catalyzed Enantioselective Allylation Reactions: Mechanistic, Structural and Preparative Studies
The method of generating chiral Lewis acids with a combination of SiCl 4 and chiral phosphoramides has been applied in the formal hetero-Diels-Alder reaction and modest to high selectivities have been obtained.
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Catalytic allylation of aldehydes mediated via the water-gas shift reaction
… the progress made in the catalytic, nucleophilic allylation of aldehydes, as mediated through the action of the Water-Gas Shift reaction (WGSR). Through this work, three main objectives were sought. Firstly, an expansion of the scope of the allyl pro-nucleophile as a way to both improve the …
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Decarboxylative Strategies in Cobalt and Metallaphotoredox Catalysis: Approaches to Aroylation, Allylation, and Strain-Driven Reactivity
Herein, the design of distinct decarboxylative strategies to access synthetically valuable molecules is described. The primary goal has been to achieve environmentally friendly cross-coupling reactions that align with the principles of green chemistry. This was successfully achieved through the use …
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New Approaches Towards the Asymmetric Allylation of the Formyl and Imino Groups via Strained Silane Lewis Acids
… presents new approaches towards the asymmetric allylation of the imino and formyl functionalities by using strained silanes as Lewis acids. Here in the Laboratory of Professor James L. Leighton, chiral homoallylic alcohols and amines are considered privileged products given their important role …
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Asymmetric Allylation of Aldehydes Catalyzed by Formamide Organocatalysts. Studies Towards The Synthesis of L- Domoic Acid Side Chain
… They are most efficiently generated by allylation of aldehydes. Classically metal-based Lewis acids are frequently used to catalyze this process. These Lewis acids are inherently sensitive to air and moisture and thus require strictly anhydrous reaction conditions. Recent developments in …
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Organic reactions catalyzed by copper(I) hydride complexes
… and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes A chemoselective hydrometalation process enables the use of easily accessible allenes as allylmetal nucleophile surrogates in imine allylation reactions. By modulating the nitrogen-protecting group, either …
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I. Synthesis of enantioenriched 3,4-disubstituted chromans through Lewis base-catalyzed carbosulfenylation II. Development and application of an indium-catalyzed allylation of unprotected carbohydrates
Submission published under a 24 month embargo labeled 'U of I Access', the embargo will last until 2026-08-01
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Fused and spiro furanones from tetronic acid synthons: Oxa and azacycles featuring the butenolide ring
… (addition – Wittig olefination) and by direct allylation of tetronic acid via Fischer esterification. 3-Allyl tetronic acids were generated by Claisen rearrangement of 4-O-allyl tetronates under microwave conditions; a subsequent Conia reaction produced the corresponding spiro cyclopropane …
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Part I: The Study Of 2-Aryl-1,3-Dithiane Derivatives As Pronucleophiles In Palladium-Catalyzed Allylic Alkylation And Propellylation Part Ii: Ligand-Free Palladium-Catalyzed Allylic Amintion Of Hydrazone Derivatives Part Iii: Synthesis Of Criegee Intermediate Precursors
… of unsaturated ketones via a one-pot allylation-oxidation protocol is also presented. Additionally, the utility of this method is demonstrated through a sequential one-pot allylation-Heck cyclization to produce asterogynin derivatives which are important bioactive compounds in …
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Part 1: Progress Toward the Total Synthesis of Platensimycin. Part 2: Aromatic Ions: Carbon-Based Nucleofuges and Chiral Cyclopropenones and Formamides
… carbon nucleofuges for the Tsuji-Trost allylation, and the use of chiral cyclopropenones and formamides for the kinetic resolution of alcohols by chlorodehydration. The first chapter describes efforts in the total synthesis of platensimycin. The synthesis attempted to use a thermal …
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Hydrocarbon Functionalization via a New Free Radical-Based Condensation Reaction
A new free radical chain process for the allylation of hydrocarbons and some other substrates utilizing substituted allyl bromides (R-H + C=C-C-Br -> R-C-C=C + HBr) has been developed. Good to excellent yields were observed in all cases. Kinetic chain measurements and competition experiments were …
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Expanding the structural diversity of discrete polymers accessible through iterative exponential growth
… was achieved through the development of a novel allylation methodology. Using alkynylation of epichlorohydrin, LiBr Finkelstein, and TfOH-promoted allylation, we have been able to prepare a monomer for 3A (number of carbons in each polymer repeat unit, excluding alkyne) IEG in just three steps. …
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Total synthesis and anticancer evaluation of all known communesin alkaloids and related complex derivatives
… derivatives, a stereoselective sulfinimine allylation, and an efficient cyclotryptamine-C3a-sulfamate synthesis by either a new silver-promoted nucleophilic amination or a rhodium-catalyzed C-H amination protocol.
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Copper(I) Hydride-Catalyzed Transformations of π-Electrophiles
… 2: Regio- and Enantioselective CuH-Catalyzed Allylation of Ketones Using Terminal Allenes An efficient method for the copper-catalyzed allylation of ketones is described using widely available terminal allenes as allylmetal surrogates. Homoallylic alcohols bearing a wide range of functional …
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Development and synthesis of novel organocatalysts
… valine, showed initial success in the catalytic allylation of aldimine with allyltrichlorosilane, producing 40% ee. Oxazoline catalysts derived from 2-pyridines have been shown to be effective activators of trichlorosilane for the reduction of ketones and ketimines. The reaction however suffered …
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Exploration of Synthetic Pathways to Quaternary Carbon Stereocenters and Fused Ring Systems via Birch Reductions
… toward cyanthiwigin F via a decarboxylative allylation as well as an enantioselective Birch – Heck sequence to make 6-5-6 and 6-6-6 carbocyclic and heterocyclic systems. In all of these examples the Birch reduction alkylation has been the key step and we have demonstrated broad applicability …
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Anion Relay Cyclopropanation and Aryl Vinyl Cyclopropane Cope Rearrangements
… application to decarboxylative and deacylative allylation reactions (DcA and DaA). This synopsis is followed by an overview of a novel anion relay cyclopropanation accomplished through a retro-Claisen activation of a nascent allylic alcohol following an initial Tsuji-Trost allylation between a …
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