Mehta, Goverdhan and Uma, R (2000) Stereoelectronic Control in Diels-Alder Reaction of Dissymmetric 1,3-Dienes. In: Accounts of Chemical Research, 33 (5). pp. 278-286.
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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, \pi-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 \pi-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.
|Item Type:||Journal Article|
|Additional Information:||Copyright for this article belongs to American Chemical Society.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||25 Jan 2005|
|Last Modified:||19 Jan 2012 06:53|
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