Stereoelectronic Control in Diels−Alder Reaction of Dissymmetric 1,3-Dienes

The Diels−Alder reaction is a widely employed protocol in which four stereogenic centers are generated in a predictable manner with olefin geometry, adjoining chiral center, and transition-state topology serving as the main controlling elements. However, when the Diels−Alder partners are in a dissym...

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Bibliographic Details
Published inAccounts of chemical research Vol. 33; no. 5; pp. 278 - 286
Main Authors Mehta, Goverdhan, Uma, R
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.05.2000
Subjects
Cyclopentanes - chemistry
Models, Molecular
Molecular Conformation
Molecular Structure
Quantum Theory
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Summary:The Diels−Alder reaction is a widely employed protocol in which four stereogenic centers are generated in a predictable manner with olefin geometry, adjoining chiral center, and transition-state topology serving as the main controlling elements. However, when the Diels−Alder partners are in a dissymmetric environment, π-face selection is determined through the interplay of steric, orbital, and electrostatic factors whose relative importance is a subject of intense debate. Several new systems have been crafted to probe the mechanistic nuances of the π-face selection. The available data have enabled us to qualitatively define a hierarchy of various stereoelectronic effects that would aid predictability of the stereochemical outcome.
Bibliography:ark:/67375/TPS-KP70RCKC-5
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content type line 23
ISSN:0001-4842
1520-4898
DOI:10.1021/ar990123s