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4092221 
Journal Article 
Stereoselectivity of the aza-Diels-Alder reaction between cyclopentadiene and protonated phenylethylimine derived from glyoxylates. A density functional theory study 
Teixeira, F; Rodriguez-Borges, JE; Melo, A; Cordeiro, MNDS 
2009 
Yes 
Chemical Physics Letters
ISSN: 0009-2614 
477 
1-3 
60-64 
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.