Conformational study of the intramolecular diels-alder reaction of a pentadienyl acrylate. Theoretical evaluation of kinetic and thermodynamic control |
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| Authors: | White Demnitz Oda Hassler Snyder |
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| Institution: | Departments of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, and Emory University, Atlanta, Georgia 30322, USA. |
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| 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. |
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