Scott E. Denmark
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View article: Stereodivergent Construction of Decalin-Based Terpenoids
Stereodivergent Construction of Decalin-Based Terpenoids Open
Thousands of highly oxygenated terpenoid natural products contain a common trans-decalin core bearing oxidized substituents in either the equatorial or axial configuration at the C(4) quaternary center. We report an expedient route to a ve…
View article: The Atroposelective Iodination of 2-Amino-6-arylpyridines Catalyzed by Chiral Disulfonimides Actually Proceeds via Brønsted Base Catalysis: A Combined Experimental and Computational Study
The Atroposelective Iodination of 2-Amino-6-arylpyridines Catalyzed by Chiral Disulfonimides Actually Proceeds via Brønsted Base Catalysis: A Combined Experimental and Computational Study Open
A thorough mechanistic investigation into the disulfonimide (DSI)-catalyzed atroposelective iodination of 2-amino-6-arylpyridines with N-iodosuccinimide is described. While initially hypothesized to proceed via Brønsted-acid catalysis thro…
View article: Data-Driven Prediction of Enantioselectivity for the Sharpless Asymmetric Dihydroxylation: Model Development and Experimental Validation
Data-Driven Prediction of Enantioselectivity for the Sharpless Asymmetric Dihydroxylation: Model Development and Experimental Validation Open
The Sharpless asymmetric dihydroxylation remains a key transformation in chemical synthesis, yet its success hides unexpected cases of lower selectivity. A chemoinformatic workflow was developed to allow data-driven analysis of the reactio…
View article: Catalytic allylation of native hexoses and pentoses in water with indium
Catalytic allylation of native hexoses and pentoses in water with indium Open
Carbohydrates are an abundant, inexpensive, and renewable biomass feedstock that could be a cornerstone for sustainable chemical manufacturing, but scalable and environmentally friendly methods that leverage these feedstocks are lacking. F…
View article: molli: A General-Purpose Python Toolkit for Combinatorial Small Molecule Library Generation, Manipulation, and Feature Extraction.
molli: A General-Purpose Python Toolkit for Combinatorial Small Molecule Library Generation, Manipulation, and Feature Extraction. Open
The construction, management and analysis of large in silico molecular libraries is critical in many areas of modern chemistry. Herein, we introduce the MOLecular LIibrary toolkit, “molli”, which is a Python 3 cheminformatics module that p…
View article: Rapid, Homogenous, B-Alkyl Suzuki–Miyaura Cross-Coupling of Boronic Esters
Rapid, Homogenous, B-Alkyl Suzuki–Miyaura Cross-Coupling of Boronic Esters Open
A rapid, anhydrous Suzuki-Miyaura cross-coupling of alkylboronic esters with aryl halides is described. Parallel experimentation revealed that the combination of AntPhos, an oxaphosphole ligand, neopentyldiol alkylboronic esters, and potas…
View article: molli: A General-Purpose Python Toolkit for Combinatorial Small Molecule Library Generation, Manipulation, and Feature Extraction.
molli: A General-Purpose Python Toolkit for Combinatorial Small Molecule Library Generation, Manipulation, and Feature Extraction. Open
The management and analysis of large in silico molecular libraries is pivotal in many areas of modern chemistry. The adoption and success of data-oriented approaches to chemical research is dependent on the ease of handling large collectio…
View article: Molecule Maker Lab Institute: Accelerating, advancing, and democratizing molecular innovation
Molecule Maker Lab Institute: Accelerating, advancing, and democratizing molecular innovation Open
Many of the greatest challenges facing society today likely have molecular solutions that await discovery. However, the process of identifying and manufacturing such molecules has remained slow and highly specialist dependent. Interfacing …
View article: Machine Learning to Develop Peptide Catalysts─Successes, Limitations, and Opportunities
Machine Learning to Develop Peptide Catalysts─Successes, Limitations, and Opportunities Open
Peptides have been established as modular catalysts for various transformations. Still, the vast number of potential amino acid building blocks renders the identification of peptides with desired catalytic activity challenging. Here, we de…
View article: ChemScraper: Leveraging PDF Graphics Instructions for Molecular Diagram Parsing
ChemScraper: Leveraging PDF Graphics Instructions for Molecular Diagram Parsing Open
Most molecular diagram parsers recover chemical structure from raster images (e.g., PNGs). However, many PDFs include commands giving explicit locations and shapes for characters, lines, and polygons. We present a new parser that uses thes…
View article: CCDC 2290421: Experimental Crystal Structure Determination
CCDC 2290421: 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 2290429: Experimental Crystal Structure Determination
CCDC 2290429: 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: A patient perspective on industrial action
A patient perspective on industrial action Open
Does strike action have a negative effect on patient-doctor relationships?
View article: Chemoinformatic Catalyst Selection Methods for the Optimization of Copper-Bis(oxazoline) Mediated, Asymmetric, Vinylogous Mukaiyama Aldol Reactions
Chemoinformatic Catalyst Selection Methods for the Optimization of Copper-Bis(oxazoline) Mediated, Asymmetric, Vinylogous Mukaiyama Aldol Reactions Open
A catalyst selection method for the optimization of an asymmetric, vinylogous Mukaiyama aldol reaction is described. A large library of commercially available and synthetically accessible copper-bis(oxazoline) catalysts was constructed in …
View article: Chemoinformatic Catalyst Selection Methods for the Optimization of Copper-Bis(oxazoline) Mediated, Asymmetric, Vinylogous Mukaiyama Aldol Reactions
Chemoinformatic Catalyst Selection Methods for the Optimization of Copper-Bis(oxazoline) Mediated, Asymmetric, Vinylogous Mukaiyama Aldol Reactions Open
A catalyst selection method for the optimization of an asymmetric, vinylogous Mukaiyama aldol reaction is described. A large library of commercially available and synthetically accessible copper-bis(oxazoline) catalysts was constructed in …
View article: Development and Validation of a Chemoinformatic Workflow for Predicting Reaction Yield for Pd-Catalyzed C-N Couplings with Substrate Generalizability
Development and Validation of a Chemoinformatic Workflow for Predicting Reaction Yield for Pd-Catalyzed C-N Couplings with Substrate Generalizability Open
A machine learning-based tool that provides conditions and predicted yields for Buchwald-Hartwig couplings from a ChemDraw™ structure input is described. The tool is built on an in-house generated experimental dataset that explores a diver…
View article: Development and Validation of a Chemoinformatic Workflow for Predicting Reaction Yield for Pd-Catalyzed C-N Couplings with Substrate Generalizability
Development and Validation of a Chemoinformatic Workflow for Predicting Reaction Yield for Pd-Catalyzed C-N Couplings with Substrate Generalizability Open
A machine learning-based tool that provides conditions and predicted yields for Buchwald-Hartwig couplings from a ChemDraw™ structure input is described. The tool is built on an in-house generated experimental dataset that explores a diver…
View article: CCDC 2131410: Experimental Crystal Structure Determination
CCDC 2131410: 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: Enantioselective Inter- and Intramolecular Sulfenofunctionalization of Unactivated Cyclic and (<i>Z</i>)-Alkenes
Enantioselective Inter- and Intramolecular Sulfenofunctionalization of Unactivated Cyclic and (<i>Z</i>)-Alkenes Open
A method for the enantioselective, Lewis base-catalyzed sulfenofunctionalization of cyclic and (Z)-alkenes is reported. The intermediate thiiranium ion generated in the presence of a selenophosphoramide catalyst is intercepted by a variety…
View article: Potassium Trimethylsilanolate-Promoted, Anhydrous Suzuki–Miyaura Cross-Coupling Reaction Proceeds via the “Boronate Mechanism”: Evidence for the Alternative Fork in the Trail
Potassium Trimethylsilanolate-Promoted, Anhydrous Suzuki–Miyaura Cross-Coupling Reaction Proceeds via the “Boronate Mechanism”: Evidence for the Alternative Fork in the Trail Open
Previous studies have shown that the critical transmetalation step in the Suzuki-Miyaura cross-coupling proceeds through a mechanism wherein an arylpalladium hydroxide complex reacts with an aryl boronic acid, termed the oxo-palladium path…
View article: Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation
Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation Open
A method for the catalytic, enantioselective, carbosulfenylation of alkenes to construct 3,4-disubstituted chromans is described. Alkene activation proceeds through the intermediacy of enantioenriched, configurationally stable thiiranium i…
View article: Lewis Base Catalyzed, Sulfenium Ion Initiated Enantioselective, Spiroketalization Cascade
Lewis Base Catalyzed, Sulfenium Ion Initiated Enantioselective, Spiroketalization Cascade Open
A Lewis base catalyzed, enantioselective sulfenocyclization of alkenes to afford [6,6]spiroketals has been developed. The method uses a chiral Lewis base catalyst with an electrophilic sulfur source to generate enantioenriched thiiranium i…
View article: Heteroaryl–Heteroaryl, Suzuki–Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate
Heteroaryl–Heteroaryl, Suzuki–Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate Open
Reaction conditions have been developed for refractory heteroaryl-heteroaryl Suzuki-Miyaura cross-couplings. The reported method employs neopentyl heteroarylboronic esters as nucleophiles, heteroaryl bromides and chlorides as the electroph…
View article: Leveraging Machine Learning for Enantioselective Catalysis: From Dream to Reality
Leveraging Machine Learning for Enantioselective Catalysis: From Dream to Reality Open
Catalyst optimization for enantioselective transformations has traditionally relied on empirical evaluation of catalyst properties. Although this approach has been successful in the past is it intrinsically limtied and inefficient. To addr…
View article: CCDC 2065452: Experimental Crystal Structure Determination
CCDC 2065452: 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 2065453: Experimental Crystal Structure Determination
CCDC 2065453: 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 2062863: Experimental Crystal Structure Determination
CCDC 2062863: 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 2062864: Experimental Crystal Structure Determination
CCDC 2062864: 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 …