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Citation
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HERO ID
4092221
Reference Type
Journal Article
Title
Stereoselectivity of the aza-Diels-Alder reaction between cyclopentadiene and protonated phenylethylimine derived from glyoxylates. A density functional theory study
Author(s)
Teixeira, F; Rodriguez-Borges, JE; Melo, A; Cordeiro, MNDS
Year
2009
Is Peer Reviewed?
Yes
Journal
Chemical Physics Letters
ISSN:
0009-2614
Volume
477
Issue
1-3
Page Numbers
60-64
DOI
10.1016/j.cplett.2009.06.009
Web of Science Id
WOS:000268329800013
Abstract
The aza-Diels-Alder reaction of cyclopentadiene with protonated (S)-phenylethylimine of methyl carboxilate was studied using density functional theory (DFT) at the B3LYP/6-31G(d) level to elucidate the reported stereoselectivity of this reaction. Four independent reaction pathways were found, all of them proceeding through a concerted, asynchronous, mechanism. Inclusion of solvent effects revealed a high exo/endo stereoselectivity that decreases with increasing temperature, in good accordance with the experimental reports. (c) 2009 Published by Elsevier B.V.
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