• Article

Conformational Study of the Intramolecular Diels-Alder Reaction of a Pentadienyl Acrylate. Theoretical Evaluation of Kinetic and Thermodynamic Control

Bibliography

White, J. D., Demnitz, F. W. J., Oda, H., Hassler, C., & Snyder, J. P. (2000). Conformational Study of the Intramolecular Diels-Alder Reaction of a Pentadienyl Acrylate. Theoretical Evaluation of Kinetic and Thermodynamic Control. Organic Letters, 2 (21), 3313 - 3316. DOI: 10.1021/ol000200f

Acrylate 4, prepared from diacetylrhamnal, underwent intramolecular Diels-Alder cycloaddition to give the thermodynamically disfavored trans-fused gamma-lactone 15 as the major product, along with two stereoisomeric cycloadducts. A computational analysis of each of the four transition states arising from 4 and the corresponding cycloadducts permits an understanding of the contrasting requirements for kinetic versus thermodynamic control of the reaction.