Brazier, John Benedict, Cavill, Julie Leanne, Elliott, Richard L., Evans, Gareth James S., Gibbs, Timothy John K., Jones, Ian Leigh, Platts, James Alexis and Tomkinson, Nicholas Charles Oliver 2009. The α-effect in cyclic secondary amines: new scaffolds for iminium ion accelerated transformations. Tetrahedron 65 (48) , pp. 9961-9966. 10.1016/j.tet.2009.10.009 |
Abstract
Five-membered secondary amine heterocycles containing an α-heteroatom were prepared and shown to be ineffective as catalysts for the iminium ion catalysed Diels–Alder reaction between cinnamaldehyde and cyclopentadiene. Their six-membered counterparts proved to be highly active catalysts. In stark contrast, the catalytic activity observed when comparing the non α-heteroatom cyclic amines proline methyl ester and methyl pipecolinate showed the five-membered ring amine was significantly more active. Concurrent density functional theoretical calculations suggest a rationale for the observed trends in reactivity, highlighting that LUMO activation through an iminium ion intermediate plays a key role in catalytic activity.
Item Type: | Article |
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Status: | Published |
Schools: | Chemistry |
Subjects: | Q Science > QD Chemistry |
Publisher: | Elsevier |
ISSN: | 0040-4020 |
Last Modified: | 04 Feb 2018 01:14 |
URI: | http://orca.cf.ac.uk/id/eprint/12549 |
Citation Data
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