4.6 Article

Theoretical Perspectives in Organocatalysis

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Rational Design of Axially Chiral Styrene-Based Organocatalysts and Their Application in Catalytic Asymmetric (2+4) Cyclizations

Si-Jia Liu et al.

Summary: A new class of axially chiral styrene-based thiourea tertiary amine catalysts with efficient synthetic route, multiple chiral elements, and multiple activating groups has been designed. These catalysts have proven to be efficient in enabling the cyclization reaction of 2-benzothiazolimines and homophthalic anhydrides with high yields and excellent stereoselectivities. The role of axially chiral styrene moiety in controlling reactivity and enantioselectivity has been elucidated through theoretical calculations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

Integrated Experimental and Computational Studies on the Organocatalytic Kinetic Resolution of β-Unfunctionalized Primary Alcohols Using a Chiral 1,2-Diamine: The Importance of Noncovalent Interactions

Naoki Sakai et al.

Summary: In this study, a novel chiral catalyst derived from (S)-proline was used to perform enantioselective kinetic resolution of beta-unfunctionalized primary alcohols with benzoyl chloride. Valuable chiral 2-substituted propan-1-ols were obtained with good enantioselectivities, and density functional theory calculations revealed the crucial role of noncovalent interactions, such as CH-pi interactions, in the enantioselectivity of the resolution.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Genetic Optimization of Homogeneous Catalysts

Ruben Laplaza et al.

Summary: The NaviCatGA package is a versatile genetic algorithm for optimizing molecular catalyst structures, demonstrated through examples to be an efficient way of accelerating catalyst discovery by bypassing combinatorial scaling issues.

CHEMISTRYMETHODS (2022)

Article Chemistry, Physical

Theoretical investigation on the mechanism and enantioselectivity of organocatalytic asymmetric Povarov reactions of anilines and aldehydes

Nan Lu et al.

Summary: The mechanism of organocatalytic asymmetric Povarov reaction of anilines and aldehydes was studied using the M06-2X functional, revealing a stepwise process with four competitive paths in the first step. The study showed that the reaction eventually leads to the formation of THQ alcohol through multiple pathways and the results were verified through Multiwfn analysis.

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

QChASM: Quantum chemistry automation and structure manipulation

Victoria M. Ingman et al.

Summary: With the advancement of computational quantum chemistry tools, larger and more complex molecular systems can now be studied. However, the analysis of these systems requires a large number of computations, making manual processes tedious and error-prone. To address this issue, a suite of free, open-source tools has been developed to automate quantum chemistry workflows.

WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE (2021)

Article Biochemistry & Molecular Biology

Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline

Maria Macia et al.

Summary: Prolinamides are well-known organocatalysts for the reduction of imines with HSiCl3, and a combination of computational calculations and experimental work was used to design optimized catalysts for a specific benchmark imine. The best results were achieved with an amide derived from 4-methoxyaniline and N-pivaloyl protected proline, making the catalyzed process almost 600 times faster than the uncatalyzed one. Mechanistic studies revealed that the formation of a supramolecular complex catalyst-HSiCl3-substrate, involving hydrogen bonding breaking and conformational changes in the prolinamide, is crucial in the overall process.

MOLECULES (2021)

Article Chemistry, Multidisciplinary

Selectivity in organocatalysis-From qualitative to quantitative predictive models

Alistair J. Sterling et al.

Summary: Recent advancements in experimental and computational techniques have revolutionized the field of chemistry, allowing for the development of predictive models to guide catalyst design. The field of organocatalysis faces challenges and promising future directions, with the combination of traditional physical organic chemistry tools and machine learning models providing a powerful approach for deeper understanding and enhanced predictive capabilities.

WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE (2021)

Article Chemistry, Multidisciplinary

Is Organic Chemistry Really Growing Exponentially?

Sara Szymkuc et al.

Summary: Organic chemistry has seen exponential growth in terms of molecules and specific reactions, but the discovery of new reaction classes/types is slower, indicating a growing reliance on known methods. The newly discovered chemistries are more complex, enabling rapid construction of complex structures in fewer steps.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Computational Discovery of Transition-metal Complexes: From High-throughput Screening to Machine Learning

Aditya Nandy et al.

Summary: This review focuses on the techniques that enable high-throughput search of transition-metal chemical space, covering the development and limitations of traditional computational chemistry along with leveraging experimental data sources. It discusses how advances in statistical modeling, artificial intelligence, and automation accelerate the discovery of lead compounds and design rules in transition-metal chemistry.

CHEMICAL REVIEWS (2021)

Article Chemistry, Multidisciplinary

Bimolecular Coupling in Olefin Metathesis: Correlating Structure and Decomposition for Leading and Emerging Ruthenium-Carbene Catalysts

Daniel L. Nascimento et al.

Summary: The study investigates the bimolecular catalyst decomposition in olefin metathesis, focusing on the susceptibility of emerging ruthenium-cyclic(alkyl)-(amino)carbene (CAAC) catalysts. Through experimental and theoretical analysis, it is found that the faster decomposition of CAAC derivatives is due to stronger trans influence weakening the Ru-py bond. This accelerated decomposition poses a challenge for fast catalyst initiation, highlighting the need to inhibit bimolecular decomposition to enhance catalyst productivity and utility in olefin metathesis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Reaction-based machine learning representations for predicting the enantioselectivity of organocatalysts

Simone Gallarati et al.

Summary: Hundreds of catalytic methods are developed annually to meet the demand for high-purity chiral compounds, but designing enantioselective organocatalysts remains a challenge. Recent research suggests that combining quantum chemical computations and machine learning can lead to advancements in asymmetric catalysis.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Machine learning meets mechanistic modelling for accurate prediction of experimental activation energies

Kjell Jorner et al.

Summary: The study introduces hybrid models combining traditional transition state modeling and machine learning to accurately predict reaction barriers, offering competitive accuracy in low-data scenarios.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Unveiling the Delicate Balance of Steric and Dispersion Interactions in Organocatalysis Using High-Level Computational Methods

Diana Yepes et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Biochemistry & Molecular Biology

Application of Halogen Bonding to Organocatalysis: A Theoretical Perspective

Hui Yang et al.

MOLECULES (2020)

Article Chemistry, Applied

Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane

Vladimir Yu. Vaganov et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Chemistry, Organic

Re-Engineering Organocatalysts for Asymmetric Friedel-Crafts Alkylation of Indoles through Computational Studies

Gabriela G. Gerosa et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Mechanism of an Organocatalytic Cope Rearrangement Involving Iminium Intermediates: Elucidating the Role of Catalyst Ring Size

Jacob N. Sanders et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Computational investigations of NHC-backbone configurations for applications in organocatalytic umpolung reactions

Kortney M. Melancon et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Article Chemistry, Physical

Improving phase-transfer catalysis by enhancing non-covalent interactions

Inigo Iribarren et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2020)

Article Chemistry, Physical

Automated exploration of the low-energy chemical space with fast quantum chemical methods

Philipp Pracht et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2020)

Article Chemistry, Multidisciplinary

Predicting retrosynthetic pathways using transformer-based models and a hyper-graph exploration strategy

Philippe Schwaller et al.

CHEMICAL SCIENCE (2020)

Article Multidisciplinary Sciences

Holistic prediction of enantioselectivity in asymmetric catalysis

Jolene P. Reid et al.

NATURE (2019)

Article Chemistry, Medicinal

DENOPTIM: Software for Computational de Novo Design of Organic and Inorganic Molecules

Marco Foscato et al.

JOURNAL OF CHEMICAL INFORMATION AND MODELING (2019)

Article Chemistry, Physical

Automatic Conformational Search of Transition States for Catalytic Reactions Using Genetic Algorithm

Hui Yang et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2019)

Article Multidisciplinary Sciences

Prediction of higher-selectivity catalysts by computer-driven worlflow and machine learning

Andrew F. Zahrt et al.

SCIENCE (2019)

Article Chemistry, Physical

Rapid virtual screening of enantioselective catalysts using CatVS

Anthony R. Rosales et al.

NATURE CATALYSIS (2019)

Article Chemistry, Physical

Globally Optimal Catalytic Fields - Inverse Design of Abstract Embeddings for Maximum Reaction Rate Acceleration

Mark Dittner et al.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2018)

Review Chemistry, Multidisciplinary

Predictive and mechanistic multivariate linear regression models for reaction development

Celine B. Santiago et al.

CHEMICAL SCIENCE (2018)

Article Chemistry, Physical

AARON: An Automated Reaction Optimizer for New Catalysts

Yanfei Guan et al.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2018)

Article Chemistry, Organic

Design and Applications of N-tert-Butyl Sulfinyl Squaramide Catalysts

Yao Li et al.

ORGANIC LETTERS (2017)

Article Multidisciplinary Sciences

Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis

Steven M. Banik et al.

SCIENCE (2017)

Article Chemistry, Multidisciplinary

Functional Mechanically Interlocked Molecules: Asymmetric Organocatalysis with a Catenated Bifunctional Bronsted Acid

Raja Mitra et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Light-Driven Enantioselective Organocatalytic β-Benzylation of Enals

Luca Dell'Amico et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Noncovalent Interactions in Organocatalysis and the Prospect of Computational Catalyst Design

Steven E. Wheeler et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

Article Chemistry, Physical

Design of Organocatalysts for Asymmetric Propargylations through Computational Screening

Analise C. Doney et al.

ACS CATALYSIS (2016)

Article Chemistry, Multidisciplinary

Computational Organic Chemistry: Bridging Theory and Experiment in Establishing the Mechanisms of Chemical Reactions

Gui-Juan Cheng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

The ORCA program system

Frank Neese

WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE (2012)

Article Chemistry, Multidisciplinary

Direct catalytic asymmetric α-amination of aldehydes

B List

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Article Chemistry, Multidisciplinary

New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction

KA Ahrendt et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)