• Article

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

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.

Citation

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

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