title: Conformational study of the intramolecular diels-alder reaction of a pentadienyl acrylate. Theoretical evaluation of kinetic and thermodynamic control
abstract: 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.
authors.affiliation: Departments of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, and Emory University, Atlanta, Georgia 30322, USA.
authors.initials: JD
authors.lastname: White
authors.initials: FW
authors.lastname: Demnitz
authors.initials: H
authors.lastname: Oda
authors.initials: C
authors.lastname: Hassler
authors.initials: JP
authors.lastname: Snyder