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View article: The asymmetric synthesis of an acyclic N-stereogenic amine
The asymmetric synthesis of an acyclic N-stereogenic amine Open
Most molecules in chemistry and biology are chiral, leading to mirror-image variants, so-called enantiomers. However, although the selective chemical synthesis of molecules in which the stereogenicity arises from a carbon atom is well-esta…
View article: Catalytic Enantioselective Diels–Alder Reaction of Dienes with Acyclic and α,β- and β,β-Disubstituted Enones
Catalytic Enantioselective Diels–Alder Reaction of Dienes with Acyclic and α,β- and β,β-Disubstituted Enones Open
Despite the wealth of methods to enantioselectively catalyze Diels-Alder reactions of α,β-unsaturated carbonyl dienophiles, until today, not a single example with an acyclic enone that is either β,β- or α,β-disubstituted has been reported.…
View article: Catalytic Asymmetric (<i>ene</i>–<i>endo</i>)-Carbonyl–Ene Type Cyclizations
Catalytic Asymmetric (<i>ene</i>–<i>endo</i>)-Carbonyl–Ene Type Cyclizations Open
The carbonyl-ene reaction between aldehydes and olefins constitutes a perfectly atom economic approach to homoallylic alcohols with concomitant C-C bond formation. However, the scope of catalytic asymmetric intermolecular versions is curre…
View article: Catalytic Asymmetric Ionic Hydrogenation of α-Alkyl Styrenes
Catalytic Asymmetric Ionic Hydrogenation of α-Alkyl Styrenes Open
Over the past two decades, chemists have made significant advances in the field of catalytic asymmetric transfer hydrogenation of various unsaturated compounds with biomimetic hydrogen donors. The reduction of carbon-carbon double bonds, h…
View article: Asymmetric Prins Cyclizations of O-Prenylated Salicylaldehydes
Asymmetric Prins Cyclizations of O-Prenylated Salicylaldehydes Open
We report the asymmetric intramolecular Prins cyclization reactions of O-prenylated salicylaldehydes to 4-chromanols. Excellent efficiencies and selectivities were herein obtained using a highly fluorinated imino-imidodiphosphate (iIDP) Br…
View article: The Overlooked Stereoisomers of the Ionizable Lipid ALC315
The Overlooked Stereoisomers of the Ionizable Lipid ALC315 Open
Lipid nanoparticles (LNPs) are a powerful delivery platform for nucleic acid therapeutics such as mRNA vaccines and gene therapies. Central to their success are ionizable lipids, which facilitate the cellular uptake and endosomal escape of…
View article: Pericyclic Umpolung in a Catalytic Asymmetric Diels–Alder Reaction of Tropone with Enol Ethers
Pericyclic Umpolung in a Catalytic Asymmetric Diels–Alder Reaction of Tropone with Enol Ethers Open
One remarkable feature of catalysis in chemical synthesis is its capacity to override substrate-imposed reactivity and selectivity. The inversion of normal reaction patterns, commonly known as Umpolung, can be divided into (1) functional g…
View article: Organocatalytic regio- and stereoselective cyclopropanation of olefins
Organocatalytic regio- and stereoselective cyclopropanation of olefins Open
As reactive intermediates and substructures of natural products and bioactive molecules, the smallest cyclic alkanes—cyclopropanes—are an attractive class of molecules for chemists. Arguably, the most general approach to their chemical syn…
View article: From Reagent to Catalyst: Dispersion-Driven Design of a General Asymmetric Transfer Hydrogenation Catalyst
From Reagent to Catalyst: Dispersion-Driven Design of a General Asymmetric Transfer Hydrogenation Catalyst Open
Even though chemists have long underappreciated the role of London dispersion in catalysis, its importance in determining a reaction course is now well recognized. Dispersion interactions have been shown to stabilize transition states and …
View article: Organocatalytic Asymmetric Synthesis of Azabicyclo[2.1.1]hexanes
Organocatalytic Asymmetric Synthesis of Azabicyclo[2.1.1]hexanes Open
The bioisosteric replacement of 2D aromatic scaffolds with sp3-rich surrogates has become an important design element in modern medicinal chemistry. Within the sp3-rich world, the azabicyclo[2.1.1]hexane (aza-BCH) scaffold stands out as a …
View article: Input to the ESPPU: The LUXE Experiment
Input to the ESPPU: The LUXE Experiment Open
This document presents an overview of LUXE (Laser Und XFEL Experiment), an experiment that will combine the high-quality and high-energy electron beam of the European XFEL with a high-intensity laser, to explore the uncharted terrain of st…
View article: Asymmetric Counteranion-Directed Halogen Bonding Catalysis
Asymmetric Counteranion-Directed Halogen Bonding Catalysis Open
Halogen bonding has been established as a promising tool in organocatalysis. Asymmetric processes are nevertheless scarce, and their applications are limited to a few studies applying chiral halogen bond donors. Herein, we combine halogen …
View article: Bronsted Acid-Catalyzed Reduction of Furans
Bronsted Acid-Catalyzed Reduction of Furans Open
Bioderived furans play a pivotal role in advancing defossilized chemical pathways. The complete reduction of furans currently relies on impractical metal-catalyzed hydrogenations at high pressures and temperatures. In addition, the Birch r…
View article: Catalytic Asymmetric Cycloaddition of Olefins with In Situ Generated <i>N</i>-Boc-Formaldimine
Catalytic Asymmetric Cycloaddition of Olefins with In Situ Generated <i>N</i>-Boc-Formaldimine Open
Chiral 1,3-amino alcohols are ubiquitous structural motifs in natural products and active pharmaceutical ingredients. We present a highly enantioselective, inverse-electron-demand hetero-Diels-Alder reaction of olefins with in situ generat…
View article: Highly Acidic Electron-Rich Brønsted Acids Accelerate Asymmetric Pictet–Spengler Reactions by Virtue of Stabilizing Cation–π Interactions
Highly Acidic Electron-Rich Brønsted Acids Accelerate Asymmetric Pictet–Spengler Reactions by Virtue of Stabilizing Cation–π Interactions Open
Electron-rich heteroaromatic imidodiphosphorimidates (IDPis) catalyze the asymmetric Pictet-Spengler reaction of N-carbamoyl-β-arylethylamines with high stereochemical precision. This particular class of catalysts furthermore provides a vi…
View article: Photocatalysis Enables the Hydroamidation of Alkenes Using Sulfonyl Azides and Hantzsch Esters
Photocatalysis Enables the Hydroamidation of Alkenes Using Sulfonyl Azides and Hantzsch Esters Open
Key words photocatalysis - hydroamidation - sulfonyl azides - alkenes - anti-Markovnikov
View article: Cooperative Photoredox and Chiral Brønsted Acid Catalysis Permits Asymmetric [2π+2σ] Cycloaddition
Cooperative Photoredox and Chiral Brønsted Acid Catalysis Permits Asymmetric [2π+2σ] Cycloaddition Open
Key words asymmetric photoredox catalysis - Brønsted acid catalysis - [2π+2σ] cycloaddition - bicyclobutanes
View article: Organocatalytic Nucleophilic Desymmetrization of P(V) Precursors
Organocatalytic Nucleophilic Desymmetrization of P(V) Precursors Open
Key words phosphorus - organocatalysis - desymmetrization - enantioselectivity - bifunctional iminophosphorane - pinacol borane
View article: Regiodivergent Radical Termination for Intermolecular Biocatalytic C–C Bond Formation
Regiodivergent Radical Termination for Intermolecular Biocatalytic C–C Bond Formation Open
Radical hydrofunctionalizations\nof electronically unbiased dienes\nare challenging to render regioselective, because the products are\nnearly identical in energy. Here, we report two engineered FMN-dependent\n“ene”-reductases (EREDs) that…
View article: Catalytic Enantioselective Wagner–Meerwein Rearrangement of Alkenyl Cycloalkanes
Catalytic Enantioselective Wagner–Meerwein Rearrangement of Alkenyl Cycloalkanes Open
Key words IDPi catalysis - aliphatic hydrocarbons - Wagner–Meerwein rearrangement
View article: Enzymatic C–H Amidation toward Stereoselective Construction of β-, γ- and δ-Lactams
Enzymatic C–H Amidation toward Stereoselective Construction of β-, γ- and δ-Lactams Open
Key words C–H amidation - myoglobin - dioxazolones - enantiodivergence - nitrene transfer
View article: CCDC 2248972: Experimental Crystal Structure Determination
CCDC 2248972: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2248971: Experimental Crystal Structure Determination
CCDC 2248971: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2248970: Experimental Crystal Structure Determination
CCDC 2248970: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Acid-Catalyzed Oxy-aminomethylation of Styrenes
Acid-Catalyzed Oxy-aminomethylation of Styrenes Open
We report a strong Brønsted acid-catalyzed three-component oxy-aminomethylation of styrenes with sym-trioxane and sulfonamides or carbamates. This transformation provides a variety of 1,3-oxazinanes in moderate to good yields under mild re…