Quantitative structure-diastereoselectivity relationships for arylsulfoxide derivatives in radical chemistry.
Quantitative structure-diastereoselectivity relationships were studied for the intermolecular radical addition of deuterium and allyltributyltin to chiral arylsulfoxides by means of multiple linear regression and artificial neural networks (ANN). The values of diastereoselectivity (% syn) of the compounds studied were well correlated with the descriptors encoding the chemical structure. Using the pertinent descriptors revealed by the regression analysis, a square correlation coefficient of 0.9577 ( s=5.3825) for the training set was obtained for the ANN model in a 2-4-1 configuration. The results obtained from this study indicate that the diastereoselectivity of arylsulfoxide derivatives is strongly dependent on the shape of the R and X groups. FIGURE General structure of alpha-sulfinyl radicals
Zahouily
Mohamed
M
Laboratoire de Catalyse, Synthèse et Environnement, Département de Chimie, Faculté des Sciences et Techniques, UFR Chimie Appliquée, B.P. 146, 20650, Mohammedia, Morocco. zahouily@voila.fr
Rayadh
Ahmed
A
Aadil
Mina
M
Zakarya
Driss
D
D002621:Chemistry / Q000379:methods; D003198:Computer Simulation; D016014:Linear Models; D016571:Neural Networks, Computer; D009930:Organic Chemicals / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship; D012044:Regression Analysis; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry
D009930:Organic Chemicals; D012451:Safrole; C005746:sulfoxide