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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| Published in | Accounts of chemical research Vol. 33; no. 5; pp. 278 - 286 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
01.05.2000
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| Subjects | |
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| Abstract | 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. |
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| AbstractList | 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. 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. 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.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. |
| Author | Uma, R Mehta, Goverdhan |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/10813872$$D View this record in MEDLINE/PubMed |
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| Snippet | The Diels−Alder reaction is a widely employed protocol in which four stereogenic centers are generated in a predictable manner with olefin geometry, adjoining... The Diels-Alder reaction is a widely employed protocol in which four stereogenic centers are generated in a predictable manner with olefin geometry, adjoining... |
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| Title | Stereoelectronic Control in Diels−Alder Reaction of Dissymmetric 1,3-Dienes |
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