Aza‐Diels–Alder reaction between cyclopentadiene and protonated N‐phenylethyliminoacetates of 8‐phenylmenthol and 8‐phenylneomenthol: a density functional theory study |
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| Authors: | Margarida S Miranda José E Rodríguez‐Borges Joaquim C G Esteves da Silva Xerardo García‐Mera |
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| Institution: | 1. Centro de Geologia da Universidade do Porto, Faculty of Science, University of Porto, , 4169‐007 Porto, Portugal;2. Centro de Investiga??o em Química, Department of Chemistry and Biochemistry, Faculty of Science, University of Porto, , 4169‐007 Porto, Portugal;3. Department of Organic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, , E‐15782 Santiago de Compostela, Spain |
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| Abstract: | The cycloaddition between glyoxylate imines possessing two chiral auxiliaries, N‐(R)‐ or N‐(S)‐1‐phenylethyl and 8‐phenylmenthyl or 8‐phenylneomenthyl, and cyclopentadiene is described. Computational calculations using density functional theory with the Becke, three‐parameter, Lee–Yang–Parr functional and the 6‐31G(d) basis set were performed to better understand the highly diastereoselective mechanism and the exo‐selectivity observed experimentally for these ionic aza‐Diels–Alder reactions. Copyright © 2011 John Wiley & Sons, Ltd. |
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| Keywords: | density functional theory exo‐selectivity ionic aza‐Diels– Alder reactions protonated quiral glyoxylate imines transition states |
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