MATEO HPTML model data

Abstract

In this Figsahre repository we release the dataset used to train/validate the MATEO: InterMolecular Amidoalkylation Theoretical Enantioselectivity Optimization Web Server. Supporting Info File: <strong>SI01_HPTML model.xlsx</strong> Content: Data used to train and validate the model. <br> Summary: The enantioselective Brønsted acid-catalyzed α-amidoalkylation reaction is a useful procedure is for the production of new drugs and natural products (products) or chiral catalysts (tools). The enantioselectivity is sensitive to many factors, from the nature of the nucleophile and the catalyst to the experimental conditions (solvent, temperature, etc.). Although computational chemistry has been used to rationalize experimental results, it is still difficult to understand the influence of different parameters (solvent, temperature, etc.) on the quantitative reaction outcome (as yield or regio- and stereoselectivities).Both experimental and computational (Quantum Chemistry) study of a large number of reactions may become costly in terms of resources and time. Thus, the development of fast-track public computational tools to predict the enantioselectivity [enantiomeric excess <em>ee</em>(%)obs] would be very useful. Furthermore, making the new tool available online could save time and experimental resources in many labs worldwide. We used an Heuristic Perturbation-Theory and Machine Learning (HPTML) algorithm to seek a predictive model with R2 = 0.91 in training and validation series has been developed. It involves a Monte Carlo sampling of&gt;100,000 pairs of query and reference reactions. In addition, the computational and experimental investigation of a new set of intermolecular α-amidoalkylation reactions using BINOL-derived <em>N</em>-trifylphosphoramides as chiral catalysts is reported as a case of study. After validation of the model, it was implementedin a web server called MATEO: InterMolecular Amidoalkylation Theoretical Enantioselectivity Optimization. This tool is available online at:https://cptmltool.rnasa-imedir.com/CPTMLTools-Web/mateo.This new user-friendly online computational tool may become useful to explore a large number of combinations of reactants, catalysts, and experimental conditions. This public tool would enable sustainable optimization of reaction conditions that could lead to the design of new catalysts, substrates, nucleophiles, and/or products.