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

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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Official URL: http://pubs.acs.org/doi/abs/10.1021/ar990123s


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
Publication: Accounts of Chemical Research
Publisher: American Chemical Society
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
URI: http://eprints.iisc.ac.in/id/eprint/2700

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